KR20230052091A - Compound, photosensitive resin composition including the same and color filter - Google Patents

Abstract

Provided are a compound represented by chemical formula 1, a photosensitive resin composition containing the compound, and a color filter manufactured by using the photosensitive resin composition. In the chemical formula 1, each substituent is as defined in the specification.

Description

Compound, photosensitive resin composition and color filter containing the same

The present disclosure relates to a compound, a photosensitive resin composition including the same, and a color filter.

A liquid crystal display device, which is one of display devices, has advantages such as light weight, thinness, low cost, low power consumption drive, and excellent bonding with integrated circuits, and its use range is expanding to notebook computers, monitors, TV images, etc. there is.

Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed; and an upper substrate on which an active circuit unit composed of a liquid crystal layer, a thin film transistor, and a storage capacitor layer and an ITO pixel electrode are formed.

In addition, the color filter may include a black matrix layer formed in a predetermined pattern on a transparent substrate to block light at a boundary between pixels; and pixel units in which a plurality of colors (typically, three primary colors of red (R), green (G), and blue (B) are arranged in a predetermined order) to form each pixel.

In the pigment dispersion method, which is one of the methods for implementing a color filter, a colored thin film is formed using a photosensitive resin composition containing a pigment as a colorant. Specifically, a series of steps including a step of coating a photosensitive resin composition on a transparent substrate provided with a black matrix to form a resin film, a step of exposing a pattern on the resin film, and a step of removing unexposed areas with a solvent and curing them with heat By repeating this, a colored thin film is formed.

However, when using the pigment dispersion method, the manufacturing process of the color filter is difficult, and the quality of the manufactured color filter is also limited. First, in order to stabilize the dispersed state of the pigment in the photosensitive resin composition to form a fine and sophisticated pattern, it is required to use a pigment having a fine particle size or use various additives such as a dispersant. In addition, storage and transportation conditions for maintaining the quality of the photosensitive resin composition in an optimal state are difficult. Moreover, in the final color filter, the limits of luminance and contrast ratio appear due to the size of the pigment particles.

Accordingly, dyes are attracting attention as a material to replace or supplement pigments. However, dyes known to date have problems in chemical resistance and chemical resistance compared to pigments, apart from excellent optical properties such as luminance and contrast ratio.

One embodiment is to provide a dye compound excellent in optical properties, chemical resistance, and chemical resistance.

Another embodiment is to provide a photosensitive resin composition containing the compound.

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.

One embodiment provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, an epoxy group, or a substituted or unsubstituted C1 to C20 alkyl group; At least one of R ¹ to R ⁴ is an epoxy group;

A is *-CO ₂ , *-SO ₃ , *-SO ₂ NSO ₂ CF ₃ , *-CONSO ₂ CF ₃ , or *-CONCOCF ₃ ;

L ¹ to L ⁴ are each independently, identically or differently, a single bond, *-O-*, a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted group consisting of N, O and S. A C2 to C20 heteroarylene group containing at least one heteroatom selected from;

L ⁵ is a substituted or unsubstituted C2 to C20 heteroarylene group containing at least one heteroatom selected from the group consisting of N, O and S;

a to d are each independently an integer of 1 to 10.

wherein any one of R ¹ and R ² is an epoxy group; The other may be a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

R ¹ is an epoxy group; *-(L ¹ ) _a -R ¹ may be represented by Formula A-1:

[Formula A-1]

In Formula A-1,

R is a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C10 alkyl;

e is an integer from 1 to 4;

L ² may be, identically or differently, a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

The R ³ and R ⁴ may each independently be a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

L ³ may be, identically or differently, a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

L ⁴ is, identically or differently, a single bond or a substituted or unsubstituted C2 to C10 heteroarylene group including one or more heteroatoms selected from the group consisting of N, O and S.

The compound represented by Formula 1 may be a compound represented by Formula 1-1 below:

[Formula 1-1]

In Formula 1-1,

R ² to R ⁴ are each independently a substituted or unsubstituted C1 to C10 alkyl group;

L ⁴ is a single bond or a substituted or unsubstituted C2 to C10 heteroarylene group containing at least one heteroatom selected from the group consisting of N, O and S;

A is *-CO ₂ , *-SO ₃ , *-SO ₂ NSO ₂ CF ₃ , *-CONSO ₂ CF ₃ , or *-CONCOCF ₃ ;

R is a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C10 alkyl;

e is an integer from 1 to 4;

The compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1-1 to 1-1-5:

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

[Formula 1-1-5]

.

.

Another embodiment provides a photosensitive resin composition comprising the compound as a dye in a colorant.

The dye may be a red dye or a magenta dye.

The colorant may further include a pigment.

The photosensitive resin composition may further include a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

The binder resin may include an acrylic binder resin, a cardo-based binder resin, or a combination thereof.

The photosensitive resin composition, based on the total amount of the photosensitive resin composition, 5% by weight to 30% by weight of the colorant; 1% to 10% by weight of the binder resin; 5% to 15% by weight of the photopolymerizable compound; 0.1 wt% to 5 wt% of the photopolymerization initiator and the balance of the solvent may be included.

The photosensitive resin composition further contains malonic acid, 3-amino-1,2-propanediol, a silane-based coupling agent containing a vinyl group or a (meth)acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof. can include

Another embodiment provides a photosensitive resin film prepared using the photosensitive resin composition.

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

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

The compound according to one embodiment is a dye that exhibits excellent optical properties, chemical resistance, chemical resistance, etc. in a photosensitive resin composition and a resin film, and can be usefully used in the manufacture of color filters.

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.

(Definition of Terms)

Unless otherwise specified herein, "substituted" to "substituted" means that one or more hydrogen atoms 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 are 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 means substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group.

In this specification, unless otherwise specified, "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, and specifically means a C6 to C20 alkoxy group. Means a C18 aryl group, "alkenyl group" means a C2 to C20 alkenyl group, specifically means a C2 to C18 alkenyl group, "alkylene group" means a C1 to C20 alkylene group, specifically C1 to C18 alkylene group, and "arylene group" means 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". Which means both are possible.

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

Unless otherwise defined in the chemical formula within this specification, if 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 the present specification, the cardo-based resin refers to a resin in which at least one functional group selected from the group consisting of Chemical Formulas 2-1 to 2-11 is included in the backbone of the resin.

In addition, unless otherwise defined in this specification, "*" means a part connected to the same or different atom or chemical formula.

(compound)

One embodiment provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, an epoxy group, or a substituted or unsubstituted C1 to C20 alkyl group; At least one of R ¹ to R ⁴ is an epoxy group;

A is *-CO ₂ , *-SO ₃ , *-SO ₂ NSO ₂ CF ₃ , *-CONSO ₂ CF ₃ , or *-CONCOCF ₃ ;

L ¹ to L ⁴ are each independently, identically or differently, a single bond, *-O-*, a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted group consisting of N, O and S. A C2 to C20 heteroarylene group containing at least one heteroatom selected from;

L ⁵ is a substituted or unsubstituted C2 to C20 heteroarylene group containing at least one heteroatom selected from the group consisting of N, O and S;

a to d are each independently an integer of 1 to 10.

As described above, in the case of using the pigment-type photosensitive resin composition, the manufacturing process of the color filter is difficult, and the quality of the manufactured color filter is also limited. In this regard, attempts have been made to realize a color filter having improved luminance and contrast ratio by introducing a dye that does not form particles instead of a pigment and preparing a photosensitive resin composition suitable for the dye.

1) The compound represented by Chemical Formula 1 corresponds to a dye that exhibits fluorescence of yellow to pink, blue, and bright colors. Compared to pigments, this can exhibit excellent optical properties in terms of luminance, contrast ratio, and the like.

2) In addition, since the compound represented by Chemical Formula 1 has a xanthene-based compound mother nucleus structure, it can exhibit excellent chemical resistance and chemical resistance. In general, since the xanthene-based compound has strong hydrophilicity, it is excellent in interaction with a binder resin having a high acid value. Accordingly, when a photosensitive resin composition, a photosensitive resin film, and a color filter are prepared together with the xanthene-based compound and the binder resin having a high acid value, the elution of the xanthene dye is suppressed, and chemical resistance equal to or higher than that of the pigment type and Chemical resistance can be expressed.

3) Furthermore, since the compound represented by Formula 1 has a structure in which the terminal is substituted with an epoxy group, durability (e.g., chemical resistance, chemical resistance etc.) is high.

Overall, the compound according to one embodiment is a dye that exhibits excellent optical properties, chemical resistance, chemical resistance, etc. in the photosensitive resin composition and resin film, and can be usefully used in the manufacture of color filters.

Hereinafter, the compound according to one embodiment will be described in more detail.

wherein any one of R ¹ and R ² is an epoxy group; The other may be a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

Specifically, R ¹ is an epoxy group; *-(L ¹ ) _a -R ¹ may be represented by Formula A-1:

[Formula A-1]

In Formula A-1, R is a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C10 alkyl; e is an integer from 1 to 4;

In addition, R ² may be a substituted or unsubstituted C1 to C10 alkyl group.

L ² may be, identically or differently, a single bond or a substituted or unsubstituted C1 to C10 alkylene group. Specifically, the L ² may be a single bond.

The R ³ and R ⁴ may each independently be a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group. Specifically, R ³ and R ⁴ may each independently be a substituted or unsubstituted C1 to C10 alkyl group.

L ³ may be, identically or differently, a single bond or a substituted or unsubstituted C1 to C10 alkylene group. Specifically, the L ³ may be a single bond.

L ⁴ is, identically or differently, a single bond or a substituted or unsubstituted C2 to C10 heteroarylene group including one or more heteroatoms selected from the group consisting of N, O and S.

The L ⁵ may be a substituted or unsubstituted C2 to C10 heteroarylene group including one or more heteroatoms selected from the group consisting of N, O and S. Specifically, L ⁵ may be a phenylene group.

a may be 3; All of b to c may be 1.

For reference, the compound represented by Chemical Formula 1 includes a resonance structure as shown in the following scheme, but in the present specification, only one structure is shown for convenience:

[scheme]

That is, the compound represented by Formula 1 may be represented by any one of the resonance structures.

The compound represented by Formula 1 may be a compound represented by Formula 1-1 below:

[Formula 1-1]

In Formula 1-1,

R ² to R ⁴ are each independently a substituted or unsubstituted C1 to C10 alkyl group;

L ⁴ is a single bond or a substituted or unsubstituted C2 to C10 heteroarylene group containing at least one heteroatom selected from the group consisting of N, O and S;

A is *-CO ₂ , *-SO ₃ , *-SO ₂ NSO ₂ CF ₃ , *-CONSO ₂ CF ₃ , or *-CONCOCF ₃ ;

R is a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C10 alkyl;

e is an integer from 1 to 4;

For example, R ² may be a hydrogen atom.

For example, R ³ and R ⁴ may each independently be a methyl group or an ethyl group.

For example, L ⁴ may be a single bond or a phenylene group.

For example, the A may be *-SO ₃ .

For example, R is a hydrogen atom, a fluorine atom, or methyl; e may be an integer of 1 to 2.

Representative examples of the compound represented by Formula 1 or the compound represented by Formula 1-1 are as follows:

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

[Formula 1-1-5]

.

.

The compound represented by Formula 1 may have maximum absorbance in a wavelength range of 450 nm to 780 nm.

(Photosensitive Resin Composition)

Another embodiment provides a photosensitive resin composition comprising the compound of the above-described embodiment as a dye in a colorant.

As it includes the compound of one embodiment described above, it exhibits excellent optical properties, chemical resistance, chemical resistance, and the like, and can be usefully used in manufacturing a color filter.

The photosensitive resin composition may include the compound of one embodiment described above as a dye in a colorant, and may further include a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

Hereinafter, each of the above components will be described in detail.

coloring agent

The colorant may include a dye, and the dye may include a compound according to one embodiment. For example, the dye may be a compound according to one embodiment.

The dye may be a red dye or a magenta dye.

The colorant may further include an organic solvent-soluble dye in addition to the above compound.

Examples of the organic solvent-soluble dye include triarylmethane-based compounds, anthraquinone-based compounds, benzylidene-based compounds, xanthene-based compounds, phthalocyanine-based compounds, azapophyrine-based compounds, and indigo-based compounds.

The colorant may further include a pigment in addition to the compound.

The pigment may include a blue pigment, a violet pigment, a red pigment, a green pigment, a yellow pigment, and the like.

Examples of the blue pigment include C.I. blue pigment 15:6, C.I. Blue Pigment 15, C.I. blue pigment 15:1, C.I. blue pigment 15:2, C.I. blue pigment 15:3, C.I. blue pigment 15:4, C.I. blue pigment 15:5, C.I. blue pigment 16, C.I. Blue Pigment 22, C.I. Blue Pigment 60, C.I. Blue Pigment 64, C.I. Blue Pigment 80 or combinations thereof.

Examples of the violet pigment include C.I. Violet Pigment 1, C.I. Violet Pigment 19, C.I. Violet Pigment 23, C.I. Violet Pigment 27, C.I. Violet Pigment 28, C.I. Violet Pigment 29, C.I. Violet Pigment 30, C.I. Violet Pigment 32, C.I. Violet Pigment 37, C.I. Violet Pigment 40, C.I. Violet Pigment 42, C.I. Violet Pigment 50 or combinations thereof.

Examples of the red pigment include C.I. Red Pigment 254, C.I. Red Pigment 255, C.I. Red Pigment 264, C.I. Red Pigment 270, C.I. Red Pigment 272, C.I. Red Pigment 177, C.I. Red Pigment 179, C.I. Red pigment 89 etc. are mentioned.

Examples of the green pigment include C.I. Green Pigment 7, C.I. Green Pigment 36, C.I. Pigment Green 58, C.I. Halogenated phthalocyanine type pigments, such as Pigment Green 59, etc. are mentioned.

Examples of the yellow pigment include C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment Yellow 150 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 dispersant 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. 15% by weight.

As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent, and the like may be used. Specific examples of the dispersant include polyalkylene glycols and esters thereof, polyoxyalkylenes, polyhydric alcohol esters, alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, and carboxylic acids. salts, alkylamide alkylene oxide adducts, alkyl amines, and the like, and these may be used alone or in combination of two or more.

For example, commercially available products of the dispersant include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK from BYK. -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 and the like from EFKA Chemical; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711, PB821, etc.

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 dispersant is included within the above range, an appropriate viscosity can be maintained and the photosensitive resin composition has excellent dispersibility, and thus optical, physical and chemical qualities can be maintained during product application.

Ethylene glycol acetate, ethyl cellosolve, propylene glycol (mono) methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like may be used as the solvent forming the pigment dispersion.

The colorant may be included in an amount of 5 wt % to 30 wt %, for example, 5 wt % to 25 wt %, based on the total amount of the photosensitive resin composition. When the colorant is included within the above range, the color reproducibility is excellent, and the curability and adhesion of the pattern are excellent.

binder resin

The binder resin may include an acrylic binder resin, a cardo-based binder resin, or a combination thereof. For example, the binder resin may be an acrylic binder resin.

The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and includes 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 combinations 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-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; 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 methacrylate. acrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc., but are not limited thereto, and may be used alone or in combination of two or more thereof. there is.

The acrylic binder resin may have a weight average molecular weight of 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 acrylic binder resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, appropriate viscosity, and excellent adhesion to a substrate when manufacturing a color filter.

The acid value of the acrylic 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 acrylic binder resin is within the above range, the pixel pattern resolution is excellent.

The cardo-based binder resin may include a repeating unit represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

R ¹¹ and R ¹² are each independently a hydrogen atom or a substituted or unsubstituted (meth)acryloyloxyalkyl group;

R ¹³ and R ¹⁴ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group;

Z ¹ is a single bond, O, CO, SO ₂ , CR ¹⁵ R ¹⁶ , SiR ¹⁷ R ¹⁸ (where R ¹⁵ to R ¹⁸ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or the following Any one of the linking groups represented by Formula 2-1 to Formula 2-11;

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

(In Chemical Formula 2-5,

R ^a is a hydrogen atom, an ethyl group, C ₂ H ₄ Cl, C ₂ H ₄ OH, CH ₂ CH=CH ₂ or a phenyl group.)

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

[Formula 2-9]

[Formula 2-10]

[Formula 2-11]

Z ² is an acid dianhydride moiety;

m1 and m2 are each independently an integer of 0 to 4.

The cardo-based binder resin may include a functional group represented by Formula 3 at at least one of both terminals.

[Formula 3]

In Formula 3,

Z ³ may be represented by Formulas 3-1 to 3-7 below.

[Formula 3-1]

(In Formula 3-1, R ^b and R ^c are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group or an ether group.)

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

(In Formula 3-5, R ^d is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, a C1 to C20 alkylamine group, or a C2 to C20 alkenylamine group.)

[Formula 3-6]

[Formula 3-7]

The cardo-based binder resin may be, for example, fluorene-containing compounds such as 9,9-bis(4-oxiranylmethoxyphenyl)fluorene; Benzene tetracarboxylic acid dianhydride, naphthalene tetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, benzophenone tetracarboxylic acid dianhydride, pyromellitic dianhydride, cyclobutanetetracarboxylic acid dianhydride, perylene tetracarboxylic acid dianhydride , anhydride compounds such as tetrahydrofurantetracarboxylic acid dianhydride and tetrahydrophthalic acid anhydride; Glycol compounds, such as ethylene glycol, propylene glycol, and polyethylene glycol; alcohol compounds such as methanol, ethanol, propanol, n-butanol, cyclohexanol, and benzyl alcohol; solvent compounds such as propylene glycol methylethyl acetate and N-methylpyrrolidone; phosphorus compounds such as triphenylphosphine; and amine or ammonium salt compounds such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, and benzyltriethylammonium chloride.

When the cardo-based binder resin is used together with the above-described acrylic binder resin, a photosensitive resin composition having excellent adhesion and high resolution and high luminance characteristics can be obtained.

The cardo-based binder resin may have a weight average molecular weight of 500 g/mol to 50,000 g/mol, such as 3,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the cardo-based binder resin is within the above range, a pattern is well formed without residue during manufacturing of the color filter, there is no loss of film thickness during development, and a good pattern can be obtained.

The cardo-based binder resin may have an acid value of 100 mgKOH/g to 140 mgKOH/g.

The binder resin may be included in an amount of 1 wt % to 10 wt %, for example, 1 wt % to 7 wt %, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent sensitivity, developability and adhesion may be obtained.

photopolymerizable compound

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

The photopolymerizable compound has the ethylenically unsaturated double bond, so that it can form a pattern having excellent chemical resistance, light resistance, and chemical resistance by causing sufficient polymerization during exposure in the pattern forming process.

Specific examples of the photopolymerizable compound 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 Latex, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylol propane tri(meth)acrylate ) acrylate, tris (meth) acryloyloxyethyl phosphate, novolak epoxy (meth) acrylate, and the like.

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

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

The photopolymerizable compound may be included in an amount of 5 wt % to 15 wt %, for example, 5 wt % to 10 wt %, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, sufficient curing occurs during exposure in the pattern forming process, resulting in excellent reliability, excellent chemical resistance, light resistance and chemical resistance of the pattern, and excellent resolution and adhesion.

photopolymerization initiator

The photopolymerization initiator is an initiator generally 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 compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloro acetophenone, p-t -Butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound 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, and the like.

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 benzyldimethylketal.

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, and the like.

Examples of the oxime-based compound 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 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-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione -2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-one oxime-O-acetate, 1-(4-phenylsulfanylphenyl)-butan-1-one oxime- O-acetate etc. are mentioned.

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

The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light, becoming excited, and then transferring the energy thereto.

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

The photopolymerization initiator may be included in an amount of 0.1 wt % to 5 wt %, for example, 0.1 wt % to 3 wt %, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, sufficient curing occurs during exposure in the pattern forming process to obtain excellent reliability, excellent chemical resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, and unreacted initiation A decrease in transmittance due to zero can be prevented.

menstruum

As the solvent, materials that are compatible with, but do not react with, the compound, pigment, binder resin, photopolymerizable compound, and photopolymerization initiator according to one embodiment 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 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; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetic acid alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic 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, 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2- monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl alkyl propionate such as methyl ethyl propionate; esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate, and 2-hydroxy-3-methyl methyl butanoate; ketonic acid esters such as ethyl pyruvate, etc., and also N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, N,N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzylethyl 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.

Among these, considering compatibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether; ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; esters such as 2-hydroxy ethyl propionate; 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 may be used.

The solvent may be included in a balance amount, for example, 40% to 80% by weight based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, the photosensitive resin composition has an appropriate viscosity, and thus processability is excellent when manufacturing the photosensitive resin film in the color filter.

Other Additives

The photosensitive resin composition may include malonic acid; 3-amino-1,2-propanediol; Silane-type coupling agent which has reactive substituents, such as a carboxyl group, a methacryloyl group, an isocyanate group, and an epoxy group; leveling agent; fluorine-based surfactants; Additives such as a radical polymerization initiator may be further included.

Examples of the silane-based coupling agent include trimethoxysilyl benzoic acid, γ-methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glyc sidoxy propyl trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more.

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

The photosensitive resin composition may further include an epoxy compound to improve adhesion to a substrate.

Examples of the epoxy compound include a phenol novolak 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 part by weight to 20 parts by weight, for example, 0.1 part 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, storability, and the like are excellent.

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

As the surfactant, a fluorine-based surfactant may be used, and examples of the fluorine-based surfactant include F-482, F-484, F-478, and F-554 of DIC, but are not limited thereto.

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 included within the above range, coating uniformity is secured, stains are not generated, 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.

(Photosensitive resin film and color filter)

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

A process of forming a pattern in the color filter is as follows.

applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing, or the like; drying the applied photosensitive resin composition to form a film of the photosensitive resin composition; exposing the film of the photosensitive resin composition to light; preparing a photosensitive resin film by developing the exposed photosensitive resin composition film with an aqueous alkali solution; and a step of heat-treating the photosensitive resin film. Since the process conditions and the like are widely known in the art, a detailed description thereof will be omitted in the present specification.

Hereinafter, the present invention will be described in more detail with reference to 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 a compound represented by Formula 1-1-1

The compound represented by Chemical Formula 1-1-1 is synthesized in three steps as described above.

4 g of Compound A (CAS No. 77545-45-0) was put into a reactor and dissolved in 30 g of 2-propanol. After adding 2.43 g of 4-Amino-m-cresol (CAS No. 2835-99-6), the mixture was stirred at 60° C. for 5 hours. The reactant was cooled and poured into 100 mL of acetone to form a precipitate. The obtained precipitate was suction filtered and further washed with acetone. The filtrate was dried to obtain Intermediate 1.

4.86 g of Intermediate 1 was added to the reactor and dissolved in 50 g of NMP. After adding 0.87 g of diethylamine (CAS No. 660-68-4) and 1.53 g of N,N-Diisopropylethylamine (CAS No. 7087-68-5), the mixture was stirred at 120°C for 8 hours. 100 g of dichloromethane was added to the reactant and extracted. The obtained organic layer was evaporated under reduced pressure after water removal with MgSO ₄ . The distilled mixture was dissolved in 10 g of dichloromethane and then added dropwise to 100 g of diethyl ether to precipitate. The precipitate obtained was suction filtered and further washed. The filtrate was dried to obtain the compound represented by Intermediate 2.

Finally, 5.2 g of Intermediate 2 was added to the reactor and dissolved in 50 g of NMP. After adding 9.14 g of epichlorohydrin (CAS No. 106-89-8) and 5.54 g of KOH, the mixture was stirred at room temperature for one day. The reactant was vacuum filtered, and the filtrate was added to 100 g of diethyl ether to precipitate. The precipitate was vacuum-filtered, dried, re-dissolved in dichloromethane, and purified through a column to obtain a compound represented by Chemical Formula 1-1-1.

[Formula 1-1-1]

Maldi-tof MS: 585 m/z

Synthesis Example 2: Synthesis of Compound Represented by Chemical Formula 1-1-2

In the same manner except for using 4-Amino-3,5-xylenol (CAS No. 3096-70-6) instead of 4-Amino-m-cresol (CAS No. 2835-99-6) of Synthesis Example 1 above. A compound represented by the following formula 1-1-2 is obtained.

[Formula 1-1-2]

Maldi-tof MS: 600 m/z

Synthesis Example 3: Synthesis of a compound represented by Formula 1-1-3

Diethylamine (CAS No. 660-68-4) of Synthesis Example 1 was replaced by N-Ethyl-o-toluidine (CAS No. 94-68-8), but the same method as in Chemical Formula 1-1-3 Obtain the indicated compound.

[Formula 1-1-3]

Maldi-tof MS: 648 m/z

Synthesis Example 4: Synthesis of Compound Represented by Chemical Formula 1-1-4

4-Amino-2-fluorophenol (CAS No. 399-96-2) was used instead of 4-Amino-m-cresol (CAS No. 2835-99-6) in Synthesis Example 1 above, and diethylamine (CAS No. 660-68-4), except for using N-Ethyl-o-toluidine (CAS No. 94-68-8), the compound represented by Formula 1-1-4 is obtained in the same manner.

[Formula 1-1-4]

Maldi-tof MS: 653 m/z

Synthesis Example 5: Synthesis of Compound Represented by Chemical Formula 1-1-5

Except for using 4-Amino-2-fluorophenol (CAS No. 399-96-2) instead of 4-Amino-m-cresol (CAS No. 2835-99-6) of Synthesis Example 1, the following formula A compound represented by 1-1-5 is obtained.

[Formula 1-1-5]

Maldi-tof MS: 591 m/z

Comparative Synthesis Example 1: Compound represented by Formula B-1

The compound represented by Formula B-1 is synthesized in two steps as described above.

4 g of Compound A (CAS No. 77545-45-0) was put into a reactor and dissolved in 30 g of 2-propanol. After adding 2.11 g of o-Toluidine (CAS No. 95-53-4), the mixture was stirred at 60°C for 5 hours. The reactant was cooled and poured into 100 mL of acetone to form a precipitate. The obtained precipitate was suction filtered and further washed with acetone. The filtrate was dried to obtain intermediate (1).

4.71 g of intermediate (1) was added to the reactor and dissolved in 50 g of NMP. After adding 0.87 g of diethylamine (CAS No. 660-68-4) and 1.53 g of N,N-Diisopropylethylamine (CAS No. 7087-68-5), the mixture was stirred at 120°C for 8 hours. The reactant was vacuum filtered, and the filtrate was added to 100 g of diethyl ether to precipitate. The precipitate was vacuum-filtered, dried, re-dissolved in dichloromethane, and purified through a column to obtain a compound represented by Formula B-1.

[Formula B-1]

Maldi-tof MS: 515 m/z

Comparative Synthesis Example 2: Compound represented by Formula B-2

A compound represented by Formula B-2 was obtained in the same manner except for using methacryloyl chloride (CAS No. 920-46-7) instead of epichlorohydrin (CAS No. 106-89-8) in Synthesis Example 1 above.

[Formula B-2]

Maldi-tof MS: 599 m/z

Comparative Synthesis Example 3: Compound represented by Formula B-3

N-Ethyl-o-toluidine (CAS No. 94-68-8) was used instead of Diethylamine (CAS No. 660-68-4) in Synthesis Example 1 above, and epichlorohydrin (CAS No. 106-89-8) Instead, a compound represented by Formula B-3 is obtained in the same manner except for using methacryloyl chloride (CAS No. 920-46-7).

[Formula B-3]

Maldi-tof MS: 661 m/z

Comparative Synthesis Example 4: Compound represented by Formula B-4

4-Amino-2-fluorophenol (CAS No. 399-96-2) was used instead of 4-Amino-m-cresol (CAS No. 2835-99-6) in Synthesis Example 1 above, and epichlorohydrin (CAS No. 106-89-8) to obtain a compound represented by Formula B-3 in the same manner except for using methacryloyl chloride (CAS No. 920-46-7).

[Formula B-4]

Maldi-tof MS: 603 m/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, after dissolving the photopolymerization initiator in a solvent, the mixture was stirred at room temperature for 2 hours, and then an acrylic binder resin and a photopolymerizable compound were added thereto and stirred at room temperature for 2 hours. Subsequently, a compound represented by Formula 1-1 (dye) and a pigment (in the form of a pigment dispersion) as a colorant were added to the obtained reactant and stirred at room temperature for 1 hour. Subsequently, a photosensitive resin composition was prepared by filtering the product three times to remove impurities.

(Unit: % by weight) Mixed raw materials content coloring agent dyes A compound represented by Formula 1-1-1 5.0 pigment dispersion Pigment Y138 pigment dispersion 15.0 alkali soluble resin (A)/(B)=15/85(w/w),
Molecular Weight (Mw)=22,000g/mol
(A): methacrylic acid
(B): benzyl methacrylate 3.5 photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 8.0 photopolymerization initiator 1,2-Octanedione 1.0 2-Dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one 0.5 menstruum cyclohexanone 37.0 Propylene Glycol Monomethyl Ether Acetate (PGMEA) 30.0 Total 100.00

Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula 1-1-2 was used instead of the compound represented by Chemical Formula 1-1-1.

Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula 1-1-3 was used instead of the compound represented by Chemical Formula 1-1-1.

Example 4

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

Example 5

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula 1-1-5 was used instead of the compound represented by Chemical Formula 1-1-1.

Comparative Example 1

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

Comparative Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula B-2 was used instead of the compound represented by Chemical Formula 1-1-1.

Comparative Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound represented by Chemical Formula B-3 was used instead of the compound represented by Chemical Formula 1-1-1.

Comparative Example 4

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

Evaluation 1: Durability measurement

Color filter specimens were prepared using the photosensitive resin compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 4.

Specifically, each photosensitive resin composition was applied to a thickness of 1 μm to 3 μm on a degreased and washed glass substrate having a thickness of 1 mm, and dried on a hot plate at 90 ° C. for 2 minutes to obtain a coating film.

The durability of each color filter specimen was evaluated in terms of chemical resistance and light resistance.

(1) Chemical resistance: For each color filter specimen, the absorption intensity at the maximum absorption wavelength (λmax) was measured. Specifically, using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer (UV-Vis-NIR spectrometer), the maximum absorption wavelength (λmax) of each color filter specimen was confirmed and the absorption intensity at that wavelength was measured. measured.

In addition, each color filter specimen was immersed in NMP (N-Methyl-2-pyrrolidone) solvent at 50 ° C. for 10 minutes, then taken out, washed with ultrapure water for 30 seconds, and then blown dry with compressed air. Then, the absorption intensity at the maximum absorption wavelength (λmax) was measured in the same manner as above.

The chemical resistance was quantified by substituting the absorbance intensity of each color filter specimen before and after solvent exposure into Equation 1 below, and the results are shown in Table 2 below.

[Equation 1]

Chemical resistance = {1 - (absorption intensity after NMP immersion)/(absorption intensity before NMP immersion)} x 100%

(2) Light fastness: For each color filter specimen, the light absorption intensity at the maximum absorption wavelength (λmax) was measured. Specifically, using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer (UV-Vis-NIR spectrometer), the maximum absorption wavelength (λmax) of each color filter specimen was confirmed and the absorption intensity at that wavelength was measured. measured.

In addition, in an exposure machine, each color filter specimen was subjected to full surface exposure under a condition of 50 mJ/cm ² , and then the absorption intensity at the maximum absorption wavelength (λmax) was measured in the same manner as described above.

The light resistance was quantified by substituting the light absorption intensity before and after exposure of each color filter specimen into Equation 2 below, and the results are shown in Table 2 below.

[Equation 2]

Light fastness = {1 - (light absorption intensity after light exposure)/(light absorption intensity before light exposure)} x 100%

chemical resistance light fastness Example 1 1.8 2.2 Example 2 1.4 1.7 Example 3 1.0 1.3 Example 4 1.2 1.5 Example 5 1.6 1.9 Comparative Example 1 29.8 30.3 Comparative Example 2 9.3 12.1 Comparative Example 3 7.6 8.7 Comparative Example 4 12.3 15.1

From Table 2, it can be seen that the photosensitive resin compositions of Examples 1 to 5 including the compound according to one embodiment as a dye have superior chemical resistance and light resistance than the photosensitive resin compositions of Comparative Examples 1 to 4. can

Evaluation 2: luminance evaluation

In the same manner as in Evaluation 1, each color filter specimen of Examples 1 to 6 and Comparative Examples 1 to 4 was prepared.

Specifically, each photosensitive resin composition was applied to a thickness of 1 μm to 3 μm on a degreased and washed glass substrate having a thickness of 1 mm, and dried on a hot plate at 90 ° C. for 2 minutes to obtain a coating film.

Each of the above coating films was exposed to light using a high-pressure mercury lamp having a dominant wavelength of 365 nm, and then dried for 5 minutes in a hot air circulation type drying oven at 200°C. Luminance of the pixel layer was measured using a spectrophotometer (MCPD3000, Otsuka electronic Co.), and the results are shown in Table 3 below.

luminance Example 1 67.1 Example 2 67.3 Example 3 67.7 Example 4 67.4 Example 5 67.5 Comparative Example 1 61.8 Comparative Example 2 64.6 Comparative Example 3 65.4 Comparative Example 4 63.3

According to Table 3, it can be seen that the photosensitive resin compositions of Examples 1 to 5 including the compound according to one embodiment as a dye show superior luminance than the photosensitive resin compositions of Comparative Examples 1 to 4. .

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and 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 (18)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom, an epoxy group, or a substituted or unsubstituted C1 to C20 alkyl group; At least one of R ¹ to R ⁴ is an epoxy group;
A is *-CO ₂ , *-SO ₃ , *-SO ₂ NSO ₂ CF ₃ , *-CONSO ₂ CF ₃ , or *-CONCOCF ₃ ;
L ¹ to L ⁴ are each independently, identically or differently, a single bond, *-O-*, a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted group consisting of N, O and S. A C2 to C20 heteroarylene group containing at least one heteroatom selected from;
L ⁵ is a substituted or unsubstituted C2 to C20 heteroarylene group containing at least one heteroatom selected from the group consisting of N, O and S;
a to d are each independently an integer of 1 to 10.
According to claim 1,
wherein any one of R ¹ and R ² is an epoxy group; A compound wherein the other is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
According to claim 2,
R ¹ is an epoxy group;
*-(L ¹ ) _a -R ¹ is a compound represented by Formula A-1:
[Formula A-1]

In Formula A-1,
R is a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C10 alkyl;
e is an integer from 1 to 4;
According to claim 3,
Wherein L ² is, identically or differently, a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
According to claim 1,
Wherein R ³ and R ⁴ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
According to claim 5,
Wherein L ³ is, identically or differently, a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
According to claim 6,
Wherein L ⁴ is, identically or differently, a single bond or a C2 to C10 heteroarylene group containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S.
According to claim 1,
A compound represented by Formula 1 is a compound represented by Formula 1-1:
[Formula 1-1]

In Formula 1-1,
R ² to R ⁴ are each independently a substituted or unsubstituted C1 to C10 alkyl group;
L ⁴ is a single bond or a substituted or unsubstituted C2 to C10 heteroarylene group containing at least one heteroatom selected from the group consisting of N, O and S;
A is *-CO ₂ , *-SO ₃ , *-SO ₂ NSO ₂ CF ₃ , *-CONSO ₂ CF ₃ , or *-CONCOCF ₃ ;
R is a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C10 alkyl;
e is an integer from 1 to 4;
According to claim 8,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 1-1-1 to 1-1-5:
[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

[Formula 1-1-5]

.
A photosensitive resin composition comprising the compound of any one of claims 1 to 9 as a dye in a colorant.
According to claim 10,
The dye is a red dye or a magenta dye photosensitive resin composition.
According to claim 10,
The photosensitive resin composition further comprises a pigment.
According to claim 10,
The photosensitive resin composition further comprises a binder resin, a photopolymerizable compound, a photopolymerization initiator and a solvent.
According to claim 13,
The binder resin is a photosensitive resin composition comprising an acrylic binder resin, a cardo-based binder resin, or a combination thereof.
According to claim 13,
The photosensitive resin composition, relative to the total amount of the photosensitive resin composition,
5% to 30% by weight of the colorant;
1% to 10% by weight of the binder resin;
5% to 15% by weight of the photopolymerizable compound;
0.1% to 5% by weight of the photopolymerization initiator and
The remaining amount of the solvent
Photosensitive resin composition comprising a.
According to claim 13,
The photosensitive resin composition further contains malonic acid, 3-amino-1,2-propanediol, a silane-based coupling agent containing a vinyl group or a (meth)acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof. A photosensitive resin composition comprising:
A photosensitive resin film prepared using the photosensitive resin composition of claim 10.
A color filter comprising the photosensitive resin film of claim 17 .