KR102603293B1 - Photosensitive resin composition comprising the same, photosensitive resin layer, color filter and cmos image sensor - Google Patents

Abstract

(A) Binder resin; (B) photopolymerizable monomer; (C) photopolymerization initiator; (D) colorants including pigments and dyes; and (E) a solvent, wherein the dye is a photosensitive resin composition consisting of a core represented by the following formula (1) and a shell surrounding the core and represented by the following formula (2), and a photosensitive resin manufactured using the photosensitive resin composition. A film, a color filter including the photosensitive resin film, and a CMOS image sensor including the color filter are provided.
[Formula 1]

[Formula 2]

(Formula 1 and Formula 2 are as defined in the specification.)

Description

Photosensitive resin composition, photosensitive resin film, color filter and CMOS image sensor {PHOTOSENSITIVE RESIN COMPOSITION COMPRISING THE SAME, PHOTOSENSITIVE RESIN LAYER, COLOR FILTER AND CMOS IMAGE SENSOR}

This description 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 next-generation detectors that can quickly transmit and receive large amounts of information and the development of new concept devices and systems. In particular, with the emergence of video processing in portable terminals, the development of ultra-miniaturized, ultra-power-saving video image sensor technology is rapidly accelerating, focusing on the existing CCD (Charge Coupled Device) and CMOS (Complementary Metal Oxide Semiconductor). am.

An image sensor is a semiconductor that converts photons into electrons that can be displayed on a display or stored in a storage device. It includes a light receiving element that converts light-receiving signals into electrical signals, a pixel circuit that amplifies and compresses the converted electrical signals, and preprocessed analog It consists of an ASIC part that converts signals into digital and processes image signals, and there are types such as CCD, CMOS, and CIS (Contact Image Sensor).

CCD and CMOS image sensors use the same light-receiving element. In the case of the CCD image sensor, the charge generated in the light-receiving part sequentially moves through MOS capacitors connected in series and is converted into voltage at the Source Follower connected to the final stage. On the other hand, in CMOS image sensors, the charge is converted into voltage in the source follower built inside each pixel and output to the outside. Looking more specifically, a CCD image sensor moves electrons generated by light to the output unit using a gate pulse, and converts the electrons generated by light into voltage within each pixel and then outputs it through several CMOS switches. This is a CMOS image sensor. The application fields of these image sensors are very wide, ranging from household products such as digital cameras and mobile phones to endoscopes used in hospitals and telescopes of artificial satellites orbiting the Earth.

As a technology trend related to CMOS image sensors, the number of pixels and sizes are decreasing to realize high image quality and miniaturization of devices. However, as the size of pixels decreases, there are limitations in manufacturing fine patterns using pigments, and the development of dyes is necessary to complement this. do. However, compared to pigments, dyes have problems in terms of fairness when manufacturing patterns. In particular, problems arise in terms of chemical resistance. This is because pigments are fine particles and have crystallinity, so they have poor solubility, so they do not dissolve in solvents such as PGMEA after baking, whereas dyes are amorphous solids, so they do not dissolve in solvents after the bake process. This is because it has the disadvantage of melting. In particular, in the case of CMOS image sensors, the content of colorant is high, so the ratio of binder resin or monomer used together is relatively low, making it difficult to improve the chemical resistance of the dye.

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

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

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

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

One embodiment of the present invention includes (A) a binder resin; (B) photopolymerizable monomer; (C) photopolymerization initiator; (D) colorants including pigments and dyes; and (E) a solvent, wherein the dye includes a core represented by Formula 1 below and a shell surrounding the core and represented by Formula 2 below.

[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, but R ¹ to R ⁸ are not hydrogen atoms at the same time,

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

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

At least one of R ³ , R ⁴ , R ⁷ and R ⁸ contains 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 integers of 0 or 1, but n1+n2 ≠ 0, n3+n4 ≠ 0,

n is an integer of 2 or more.

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 of R ³ , R ⁴ , R ⁷ and R ⁸ may each be represented by the following formula (3).

[Formula 3]

In Formula 3 above,

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 end. At this time, Formula 1 may be expressed as Formula 1-1 or Formula 1-2 below.

[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 with each other to form a ring, or R ³ and R ⁴ may be fused with each other to form a ring,

R ¹ to R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,

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

n5 and n6 are each independently integers 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 containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,

n5 and n6 are each independently integers 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. At this time, Chemical Formula 1 may be expressed as 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 containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,

n5 and n6 are each independently integers 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. At this time, Chemical Formula 1 may be expressed as 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,

Neither R ⁶ nor R ⁸ contain a siloxane group,

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

n5 and n6 are each independently integers of 0 or 1.

The core represented by Formula 1 may have a maximum absorption wavelength 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 of the following 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 used 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 implementation provides a CMOS image sensor including the color filter.

Details of other aspects of the invention are included in the detailed description below.

The core-shell compound according to one embodiment has excellent chemical resistance in itself and can maintain excellent chemical resistance even after curing and thermal processes, and the photosensitive resin composition containing this as a dye is capable of forming fine patterns, and is capable of forming CMOS 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 presented as an example, and the present invention is not limited thereby, and the present invention is only defined by the scope of the claims to be described later.

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

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 refers to a C1 to C18 cycloalkyl group, “alkoxy group” refers to a C1 to C20 alkoxy group, specifically refers to a C1 to C18 alkoxy group, and “aryl group” refers to a C6 to C20 aryl group, specifically refers to a C6 to C20 aryl group. means a C18 aryl group, “alkenyl group” means a C2 to C20 alkenyl group, specifically means a C2 to C18 alkenyl group, and “alkylene group” means a C1 to C20 alkylene group, specifically a C1 to C18 alkylene group, and “arylene group” refers to a C6 to C20 arylene group, specifically, a C6 to C16 arylene group.

Unless otherwise specified herein, “(meth)acrylate” means both “acrylate” and “methacrylate”, and “(meth)acrylic acid” means “acrylic acid” and “methacrylic acid”. This means that both are possible.

Unless otherwise defined herein, “combination” means mixing or copolymerization. Additionally, “copolymerization” refers to block copolymerization to random copolymerization, and “copolymer” refers to block copolymerization to random copolymerization.

In this specification, the siloxane group refers to any functional group containing a Si-O bond, such as *-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 referred to in this specification.

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

Additionally, unless otherwise defined in the specification, “*” means a portion connected to the same or different atom or chemical formula.

One embodiment includes (A) a binder resin; (B) photopolymerizable monomer; (C) photopolymerization initiator; (D) colorants including pigments and dyes; and (E) a solvent, wherein the dye includes a core represented by Formula 1 below and a shell surrounding the core and represented by Formula 2 below.

[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, but R ¹ to R ⁸ are not hydrogen atoms at the same time,

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

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

At least one of R ³ , R ⁴ , R ⁷ and R ⁸ contains 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 integers of 0 or 1, but n1+n2 ≠ 0, n3+n4 ≠ 0,

n is an integer of 2 or more.

coloring agent

In color filters manufactured from pigment-type photosensitive resin compositions, there are problems with color mixing and thinning of the color filter due to the size of the pigment particles. Additionally, in the case of color imaging devices for image sensors, smaller dispersed particles are required to form fine patterns. In order to meet such demands, efforts have been made for a long time to increase resolution by introducing dyes that do not form particles instead of pigments and manufacturing photosensitive resin compositions suitable for dyes.

The photosensitive resin composition according to one embodiment includes green dye and pigment that are used in a color filter for a CMOS image sensor. As the size of the pixel decreases, there are limitations in manufacturing fine patterns using pigments, and the development of dyes is necessary to compensate for this. Dyes have problems in terms of processability when manufacturing patterns compared to pigments, and are particularly inferior in chemical resistance. It was very difficult to form fine patterns after curing and heat processing. In addition, when the dye, which is a colorant, is included in only a small amount compared to the total amount of the composition, it is not a big problem even if the chemical resistance of the dye itself is slightly inferior. However, in the case of a photosensitive resin composition for a CMOS image sensor, the dye is used in excess (approximately compared to the total amount of the photosensitive resin composition). Since it is contained in an amount of 15% to 30% by weight, for example, about 20% to 30% by weight, there is a great need to develop a dye that has excellent chemical resistance.

After experiencing numerous trials and errors, the inventors of the present invention synthesized a core-shell compound by controlling and introducing a siloxane group into the squarylium-based compound forming the core under specific conditions and surrounding the core with a shell. The core-shell compound according to one embodiment has excellent chemical resistance on its own, and the photosensitive resin composition containing it together with a pigment and an excessive amount of green dye does not have a significant decrease in chemical resistance even after curing and thermal processes, and thus 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 the following formula (3).

[Formula 3]

In Formula 3 above,

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 end. 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 the following Formula 1-1 or Formula 1-2, but is not necessarily 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 with each other to form a ring, or R ³ and R ⁴ may be fused with each other to form a ring,

R ¹ to R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,

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

n5 and n6 are each independently integers 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 containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,

n5 and n6 are each independently integers 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. 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 the following Formula 1-3, 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 containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,

n5 and n6 are each independently integers 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. 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 the following Formulas 1-4, 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,

Neither R ⁶ nor R ⁸ contain a siloxane group,

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

n5 and n6 are each independently integers of 0 or 1.

The core represented by Formula 1 may include 2, 4, or 6 siloxane groups. The core represented by Formula 1, which has 1, 3, or 5 siloxane groups, is difficult to synthesize (low yield) due to its structure, and even if the actual synthesis is successful, it is expensive to apply it to an actual line, so it is not economical. Not desirable.

In addition, the core represented by Formula 1 is superior in terms of chemical resistance when the number of siloxane groups is 6 compared to when the number of siloxane groups is 4, and when the number of siloxane groups is 4 is superior to 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 better than 4, and 6 is better than 4.

On the other hand, in the core represented by Formula 1, the case where the number of siloxane groups is 2 is superior to the case where the number of siloxane groups is 4 in terms of solubility of the compound, and the case where the number of siloxane groups is 4 is superior to the case where the number of siloxane groups is 6. great. That is, if only the solubility aspect of the compound is considered, the number of siloxane groups in the core structure represented by Formula 1 is better than 4, and 2 is better than 4.

Meanwhile, in the core represented by Formula 1, when the number of siloxane groups is 1, not only is synthesis difficult as described above, but the chemical resistance is lower than when the number of siloxane groups is 2, so the core represented by Formula 1 The core preferably contains two or more siloxane groups.

That is, it may be most desirable for the core represented by Formula 1 to have four siloxane groups, considering both chemical resistance and solubility of the compound.

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

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 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, a photosensitive resin composition including the dye according to the above embodiment is provided.

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, producing a green color for high-transmission CIS. It may be suitable for filter implementation. That is, the photosensitive resin composition may be used 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 photopolymerization initiator, and a solvent.

The dye according to one embodiment may be included in an amount of 15% by weight to 30% by weight, for example, 20% by weight to 30% by weight, based on the total amount of the photosensitive resin composition. When the dye according to one embodiment is included in the above range, not only can color gamut and contrast ratio be improved, but it can also be applied to a CMOS image sensor .

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

The yellow pigment is classified as C.I. in the color index. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, etc. can be mentioned, and these can be used alone or in a mixture of two or more types.

The green pigment is classified as C.I. in the color index. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59 and the like can be mentioned, and these can be used alone or in a mixture of two 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 dispersant for uniformly dispersing the pigment within the solvent.

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

As the dispersant, a nonionic dispersant, an anionic dispersant, a cationic dispersant, etc. may be used. Specific examples of the dispersant include polyalkylene glycol and its esters, polyoxyalkylene, polyhydric alcohol 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, etc. may be used, and these may be used alone or in combination of two or more.

Examples of commercially available dispersants include BYK's DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, and 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; Zeneka's Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000, etc.; Alternatively, there are Ajinomoto's PB711 and PB821.

The dispersant may be included in an amount of 1% to 20% by weight based on the total amount of the pigment dispersion. When the dispersant is included within the above range, appropriate viscosity can be maintained and the dispersibility of the photosensitive resin composition is excellent, and thus optical, physical and chemical quality can be maintained when the product is applied.

Solvents for forming the pigment dispersion include ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, and propylene glycol methyl ether.

The pigment dispersion may be included in an amount of 15% to 60% by weight, for example, 30% to 50% by weight, based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous to secure the process margin and the color reproduction rate 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 containing 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% to 50% by weight, for example, 10% to 40% by weight, based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzylmethyl ether; Methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxy butyl (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 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; These can be mentioned, and these can be used alone or in a mixture 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 methacrylate Examples include, but are not limited to, acrylate copolymers, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymers, and these may be used alone or in combination of two or more types. there is.

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, an appropriate viscosity, and excellent adhesion to the 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% to 30% by weight, for example, 1% to 20% by weight, based on the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, developability is excellent when manufacturing a color filter, crosslinking property is improved, and excellent surface smoothness can be obtained.

photopolymerizable monomer

The photopolymerizable monomer may be a mono- or multi-functional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

By having the ethylenically unsaturated double bond, the photopolymerizable monomer can form a pattern with excellent heat resistance, light resistance, and chemical resistance by sufficiently polymerizing it upon exposure to light in the pattern formation 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, and 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( Meta)acrylate, tris(meth)acryloyloxyethyl phosphate, novolak epoxy (meth)acrylate, etc. are mentioned.

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® , and M- ^114® manufactured by Toagosei Chemical Co., Ltd.; Nippon Kayaku Co., Ltd.'s KAYARAD TC-110S ^® , KAYARAD TC-120S ^® , etc.; Examples include V-158 ^® and V-2311 ^® manufactured by Osaka Yuki Chemical Co., Ltd. Examples of the above-mentioned difunctional ester of (meth)acrylic acid include Aronics M-210 ^® , M-240 ^® , and M-6200 ^® manufactured by Toagosei Chemical Co., Ltd.; Nihon Kayaku Co., Ltd.'s KAYARAD HDDA ^® , HX-220 ^® , R-604 ^® , etc.; Examples include V-260 ^® , V-312 ^® , and V-335 HP ^® manufactured by Osaka Yuki Chemical Engineering Co., Ltd. Examples of the trifunctional ester of (meth)acrylic acid include Aronics M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , and M manufactured by Toagosei Chemical Co., Ltd. -710 ^® , M-8030 ^® , M-8060 ^® , etc.; Nippon Kayaku Co., Ltd.'s KAYARAD TMPTA ^® , DPCA-20 ^® , Dong-30 ^® , Dong-60 ^® , Dong-120 ^® , etc.; Examples include V-295 ^® , Dong-300 ^® , Dong-360 ^® , Dong-GPT ^® , Dong-3PA ^® , and Dong-400 ^® manufactured by Osaka Yuki Kayaku Kogyo Co., Ltd. The above products can be used alone or in combination of two or more types.

The photopolymerizable monomer may be used after being treated with an acid anhydride to provide better developability.

The photopolymerizable monomer may be included in an amount of 1% to 15% by weight, for example, 1% to 10% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included within the above range, sufficient curing occurs during exposure to light in the pattern formation process, resulting in excellent reliability and excellent developability in an alkaline developer.

photopolymerization initiator

The photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, 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 compounds include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloro acetophenone, p-t -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc.

Examples of the benzophenone-based compounds include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

Examples of the thioxanthone-based compounds include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone, etc. can be 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 compounds 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.

Examples of the oxime-based compounds include O-acyloxime-based compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 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 compounds 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)-octan-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butane-1-oneoxime-O- Acetate, etc. can be mentioned.

In addition to the above compounds, the photopolymerization initiator may include carbazole-based compounds, diketone-based compounds, sulfonium borate-based compounds, diazo-based compounds, imidazole-based compounds, biimidazole-based compounds, and fluorene-based compounds.

The photopolymerization initiator may be used together with a photosensitizer that absorbs light, becomes excited, and then transmits the energy to cause a chemical reaction.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, etc. can be mentioned.

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 during the pattern formation process to obtain excellent reliability, the heat resistance, light resistance, and chemical resistance of the pattern are excellent, resolution and adhesion are also excellent, and there is no damage from unreacted initiators. Deterioration of transmittance can be prevented.

menstruum

The solvent may be a material that is compatible with but does not react with the dye, pigment, binder resin, photopolymerizable monomer, and photopolymerization initiator.

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 methyl ethyl 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; Alkyl oxyacetic acid 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 methyl 3-oxypropionate and ethyl 3-oxypropionate; 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 propionate esters such as methyl 2-oxy-2-methyl propionate, ethyl 2-oxy-2-methyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2- monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl alkyl propionate such as ethyl methyl propionate; esters such as ethyl 2-hydroxy propionate, 2-hydroxy-2-methyl ethyl propionate, ethyl hydroxy acetate, and 2-hydroxy-3-methyl methyl butanoate; Keto acid esters such as ethyl pyruvate, and others include 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. High boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate can be mentioned.

Among these, 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 the remaining amount, for example, 10 wt% to 50 wt%, for example, 10 wt% to 40 wt%, based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has an appropriate viscosity, thereby improving processability when manufacturing a color filter.

Other additives

The photosensitive resin composition according to one embodiment may further include an epoxy compound to improve adhesion to the substrate.

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 to 20 parts by weight, for example, 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the above range, adhesion, storage, etc. are excellent.

In addition, the photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, methacryloyl group, isocyanate group, or epoxy group 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, and γ glycidoxy propyl trimethoxysilane. Examples include methoxysilane, β-epoxycyclohexyl)ethyltrimethoxysilane, and these can be used alone or in combination of two or more types.

The silane coupling agent may be included in an amount of 0.01 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, storage, etc. are excellent.

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

Examples of the surfactant include BM-1000 ^® and BM-1100 ^® from BM Chemie; Mecha pack F 142D ^® , F 172 ^® , F 173 ^® , F 183 ^® , etc. from Dai Nippon Inki Chemicals Co., Ltd.; Prorad FC-135 ^® , FC-170C ^® , FC-430 ^® , FC-431 ^® , etc. from Sumitomo 3M Co., Ltd.; Asahi Grass Co., Ltd.'s Saffron S-112 ^® , S-113 ^® , S-131 ^® , S-141 ^® , S-145 ^® , etc.; Fluorine-based surfactants commercially available under names such as SH-28PA ^® , Dong-190 ^® , Dong-193 ^® , SZ-6032 ^® , and SF-8428 ^® from Toray Silicone Co., Ltd. can be used.

The surfactant may be used in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, coating uniformity is ensured, stains do not occur, and wetting on the glass substrate is excellent.

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

According to another embodiment, a photosensitive resin film manufactured using the photosensitive resin composition according to the above embodiment is provided.

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

The pattern formation process within the color filter is as follows.

A process of applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing, etc.; A step of drying the applied photosensitive resin composition to form a photosensitive resin composition film; A process of exposing the photosensitive resin composition film; A process of developing the exposed photosensitive resin composition film with an aqueous alkaline solution to produce a photosensitive resin film; and a step of heat treating the photosensitive resin film. Since the above process conditions are widely known in the field, detailed description will be omitted in this specification.

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

Hereinafter, the present invention will be described in more detail through examples. However, 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) is added to toluene (300 mL) and butanol (300 mL), refluxed, and the resulting water is removed using a Dean-stark distillation device. 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 chloroform solvent, Pyridine-2,6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL chloroform, and dissolved in 5 mL of chloroform at room temperature. Dropped simultaneously 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 50mL tetrahydrofuran solvent, tetrabutylammonium fluoride (11 mmol) was added at room temperature. After 30 minutes, the mixture was separated by column chromatography to obtain the compound represented by Intermediate 1-3.

Synthesis Example 4: Synthesis of the compound represented by formula A

After reacting the compound represented by Intermediate 1-3 (5 mmol) and sodium hydride (15 mmol) in 25mL N,N-dimethylformamide solvent for 1 hour, (3-Iodopropyl)trimethoxysilane (15 mmol) was added and the mixture was heated to 50°C. Raise the temperature. After 8 hours, the mixture 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-hexyl)-phenyl-amine instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-2 The compound represented by Intermediate 2-1 was obtained by synthesizing in the same manner as in Synthesis Example 1, except that -propoxy-ethyl)-phenyl-amine was used.

(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 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 synthesis in the same manner as 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

A compound represented by the following formula B was obtained by synthesis 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 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 synthesis in the same manner as 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 synthesis in the same manner as 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 the compound represented by formula C

A compound represented by the following formula C was obtained by synthesis in the same manner as 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)

Instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine, [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 synthesis in the same manner as 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 synthesis in the same manner as 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

A compound represented by the following formula D was obtained by synthesis in the same manner as 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 The compound represented by Intermediate 5-1 was obtained by synthesizing in the same manner as in Synthesis Example 1, except that -methyl-hexyl)-phenyl-amine was used.

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

The compound represented by Intermediate 5-2 was obtained by synthesis in the same manner as 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 synthesis 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

A compound represented by the following formula E was obtained by synthesis in the same manner as 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)

Instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine, [2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-phenyl- The compound represented by Intermediate 6-1 was obtained by synthesis 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 synthesis in the same manner as 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 synthesis 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 the compound represented by formula F

A compound represented by the following formula F was obtained by synthesis in the same manner as 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)

Instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine, [4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-butyl]-phenyl- The compound represented by Intermediate 7-1 was obtained by synthesis in the same manner as 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 synthesis in the same manner as 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 synthesis 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

A compound represented by the following formula G was obtained by synthesis in the same manner as 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 The compound represented by Intermediate 8-1 was obtained by synthesis in the same manner as in Synthesis Example 1, except that -(tert-butyl-dimethyl-silanyloxy)-phenyl]-phenyl-amine was used.

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

The compound represented by Intermediate 8-2 was obtained by synthesis in the same manner as 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)

After dissolving the compound represented by Intermediate 8-2 (5 mmol) in 50mL tetrahydrofuran solvent, tetrabutylammonium fluoride (22 mmol) was added at room temperature. After 30 minutes, the mixture 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

After reacting the compound represented by Intermediate 8-3 (5 mmol) and sodium hydride (30 mmol) in 25mL N,N-dimethylformamide solvent for 1 hour, (3-Iodopropyl)trimethoxysilane (30 mmol) was added and the mixture was heated to 50°C. Raise the temperature. After 8 hours, separation is performed 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)

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

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

The compound represented by Intermediate 9-2 was obtained by synthesis in the same manner as 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 synthesis in the same manner as 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

A compound represented by the following formula (I) was obtained by synthesis in the same manner as 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)

Instead of [4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-(1-methyl-hexyl)-phenyl-amine, [2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl- 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 synthesis in the same manner as 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 50mL tetrahydrofuran solvent, tetrabutylammonium fluoride (44 mmol) was added at room temperature. After 30 minutes, the mixture 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 in 25 mL N,N-dimethylformamide solvent for 1 hour, then (3-Iodopropyl)trimethoxysilane (45 mmol) was added and the mixture was heated to 50°C. Raise the temperature. After 8 hours, separation is performed 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 synthesis in the same manner as 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 synthesis in the same manner as 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 the compound represented by formula K

A compound represented by the following formula (K) was obtained by synthesis in the same manner as Synthesis Example 39, except that the compound represented by Intermediate 11-3 was used instead of the compound represented by Intermediate 10-3.

[Formula K]

Maldi-tof MS: 2217.0 m/z

Comparative Synthesis Example 1: Synthesis of the 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 using a Dean-stark distillation device. After stirring for 12 hours, the reactant is distilled under reduced pressure and purified by column chromatography to obtain a squaylium-based compound. After dissolving this compound (5 mmol) in 600 mL chloroform solvent, Pyridine-2,6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL chloroform and added dropwise simultaneously for 5 hours at room temperature. After 12 hours, it is distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula C-1.

[Formula C-1]

Maldi-tof MS: 1175.5 m/z

Comparative Synthesis Example 2: Synthesis of the 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 device. After stirring for 12 hours, the green reactant is distilled under reduced pressure and purified by column chromatography to obtain an asymmetric squylium-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 added dropwise simultaneously at room temperature for 5 hours. After 12 hours, it is distilled under reduced pressure and separated by column chromatography to obtain a compound represented by the following formula C-2.

[Formula C-2]

Maldi-tof MS: 1088.48 m/z

Comparative Synthesis Example 3: Synthesis of the compound represented by formula C-3

(1) Add 2,4-dimethyldiphenylamine (10 mol), 1,2-epoxycyclohexane (12 mol), and sodium hydride (12 mol) to N,N-dimethylformamide and heat to 90°C for 24 hours. Stirred for an hour. 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 water produced is removed using a Dean-Stark distillation device. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain the core compound represented by the following formula.

(4) After dissolving the core compound (5 mmol) in 600 mL chloroform solvent, triethylamine (50 mmol) was added. Dissolve 2,6-pyridinedicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) in 60 mL 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 the formula C-3.

[Formula C-3]

Maldi-tof MS: 1230.59m/z

(Synthesis of photosensitive resin composition)

Example 1

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

Specifically, the photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 2 hours, then a binder resin and a photopolymerizable monomer were added thereto and stirred at room temperature for 2 hours. Next, the compound prepared in Synthesis Example 4 (compound represented by Chemical 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: weight%) Mixed raw materials 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)=22,000g/mol
(A): Methacrylic acid
(B): Benzyl methacrylate 3 photopolymerizable monomer Dipentaerythritol hexaacrylate (DPHA) 2.5 photopolymerization initiator 1,2-octanedione 0.3 menstruum Propylene Glycol Monomethyl Ether Acetate (PGMEA) 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 (the compound represented by Formula B) was used instead of the compound of Synthesis Example 4 (the 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 (the compound represented by the formula C) was used instead of the compound of Synthesis Example 4 (the compound represented by the 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 (the compound represented by Formula D) was used instead of the compound of Synthesis Example 4 (the 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 (the compound represented by the formula F) was used instead of the compound of Synthesis Example 4 (the compound represented by the 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 (the compound represented by the formula G) was used instead of the compound of Synthesis Example 4 (the compound represented by the 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 (the compound represented by the formula H) was used instead of the compound of Synthesis Example 4 (the compound represented by the 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 (the compound represented by Formula I) was used instead of the compound of Synthesis Example 4 (the 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 (the compound represented by Formula J) was used instead of the compound of Synthesis Example 4 (the 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 (the compound represented by Formula K) was used instead of the compound of Synthesis Example 4 (the 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 (the compound represented by the formula C-2) was used instead of the compound of Synthesis Example 4 (the compound represented by the 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 chemical resistance of compositions

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

Afterwards, the prepared color filter specimen was immersed in the PGMEA solution at room temperature for 5 minutes, and the 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 composition (Examples 1 to 11) according to one embodiment has excellent chemical resistance and is very suitable for use in a CMOS image sensor.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and can be implemented with various modifications within the scope of the claims, the detailed description of the invention, and the accompanying drawings, and this also applies to the present invention. It is natural that it falls within the scope of the invention.

Claims (17)

(A) Binder resin;
(B) photopolymerizable monomer;
(C) photopolymerization initiator;
(D) colorants including pigments and dyes; and
(E) Solvent
Including,
The dye is a photosensitive resin composition consisting of a core represented by the following formula (1) and a shell surrounding the core and represented by the following formula (2):
[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, but R ¹ to R ⁸ are not hydrogen atoms at the same time,
R ¹ and R ² may be fused with each other to form a ring, or R ³ and R ⁴ may be fused with each other to form a ring,
At least one of R ¹ , R ² , R ⁵ and R ⁶ contains a siloxane group at the terminal,
At least one of R ³ , R ⁴ , R ⁷ and R ⁸ contains 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 integers of 0 or 1, but n1+n2 ≠ 0, n3+n4 ≠ 0,
n is an integer of 2 or more.
According to paragraph 1,
A photosensitive resin composition wherein the substituent including a siloxane group at the terminal includes an ether linking group (*-O-*).
According to paragraph 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 formula (3):
[Formula 3]

In Formula 3 above,
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 paragraph 1,
A photosensitive resin composition wherein 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 each independently include a siloxane group at an end.
According to paragraph 1,
A photosensitive resin composition wherein 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 each independently include a siloxane group at the terminal.
According to paragraph 1,
A photosensitive resin composition wherein 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 each independently include a siloxane group at the terminal.
According to paragraph 4,
The above Chemical Formula 1 is a photosensitive resin composition represented by the following Chemical 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 with each other to form a ring, or R ³ and R ⁴ may be fused with each other to form a ring,
R ¹ to R ⁴ , R ⁶ and R ⁸ all do not contain a siloxane group,
R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,
n5 and n6 are each independently integers of 0 or 1.
According to paragraph 4,
The above Chemical Formula 1 is a photosensitive resin composition represented by the following Chemical Formula 1-2:
[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 containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,
n5 and n6 are each independently integers of 0 or 1.
According to clause 5,
The above Chemical Formula 1 is a photosensitive resin composition represented by the following Chemical 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 containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,
n5 and n6 are each independently integers of 0 or 1.
According to clause 6,
The above Chemical Formula 1 is a photosensitive resin composition represented by the following Chemical Formulas 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,
Neither R ⁶ nor R ⁸ contain a siloxane group,
R ¹ to R ⁵ and R ⁷ are each independently a C1 to C20 alkyl group containing a siloxane group at the terminal or a C1 to C20 alkoxy group containing a siloxane group at the terminal,
n5 and n6 are each independently integers of 0 or 1.
According to paragraph 1,
The core represented by Formula 1 is a photosensitive resin composition having a maximum absorption wavelength of 610 nm to 640 nm.
According to paragraph 1,
The shell represented by Formula 2 is a photosensitive resin composition represented by the following Formula 2-1.
[Formula 2-1]

According to paragraph 1,
The dye is a photosensitive resin composition represented by any one of the following 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 paragraph 1,
A photosensitive resin composition wherein the dye is a green dye.
A photosensitive resin film comprising the photosensitive resin composition of any one of claims 1 to 14.
A color filter comprising the photosensitive resin film of claim 15.
A CMOS image sensor including the color filter of claim 16.