KR20170129416A - triazine derivatives having a triazine group, pigment dispersing aid containing the same and pigment dispersion containing the same - Google Patents

Abstract

The present invention relates to a triazine derivative, a pigment dispersion preparation containing the same, and a pigment dispersion containing the same. The triazine derivative of the present invention ensures high heat resistance and excellent dispersibility, thereby increasing storage stability and dispersibility of pigment dispersions containing the same. Accordingly, colored photosensitive resin compositions containing the pigment dispersion of the present invention show superior optical features such as brightness and contrast.

Description

[0001] The present invention relates to a triazine derivative having a triazine functional group, a pigment dispersion preparation containing the triazine derivative, a pigment dispersing aid containing the same and a pigment dispersion containing the same,

The present invention relates to a triazine derivative, a pigment dispersion aid containing the same, and a pigment dispersion containing the same, and more particularly, to a triazine derivative having a high affinity with a pigment and high heat resistance to exhibit excellent dispersibility and storage stability, A pigment dispersion containing a pigment dispersing aid, and a pigment dispersion.

A color filter used in a liquid crystal display is manufactured by forming patterns of three primary colors, that is, red, green and blue on a glass substrate.

The process of producing a color pattern includes uniformly applying a photosensitive coloring composition containing a coloring agent corresponding to each color pixel on a substrate, heating-drying the applied composition to form a film Selectively exposing and drying the dried film using a mask of a desired shape, and heating and curing the developed film.

The coloring agent of the photosensitive resin composition used in such a process generally uses a pigment.

Recently, in accordance with the trend of display technology innovation, a pigment dispersion having characteristics of high transmittance (luminance) and high contrast is required to save power of a display for a liquid crystal display device, and a color gamut is expanded The goal is to achieve a high color recall rate.

In order to achieve such a goal, the pigment concentration must be high, but a high level of pigment dispersion is required because the high concentration of the pigment degrades the storage stability of the pigment dispersion itself and the storage stability and pattern fairness even when it is made into a resist .

In addition to pigments, dispersants, and resins, a pigment dispersion aid that stabilizes the pigment surface is used as the pigment dispersion. The pigment dispersing aid can stabilize the surface of the pigment to prevent the storage stability of the pigment dispersion and the sublimation of the pigment, and further, when the pigment dispersion aid is applied to the surface treatment of the pigment, the pigment surface is more stabilized, Can be dispersed.

However, the conventional pigment dispersing aid has a structure different from that of the pigment as a whole by applying substitution groups to the same parent skeleton as the pigment, so that the color spectrum of the pigment and the conventional pigment dispersing aid is changed, . As a result, the luminance of the image displayed on the display is lowered, which does not meet the development target of the current display aiming at low power.

Conventionally, a pigment dispersant and a dispersing aid having a triazine ring as a parent skeleton are known, but the known structure is limited to a role as a pigment surface treatment agent, and a pigment dispersion auxiliary having still improved properties is required.

Korean Patent Publication No. 10-2012-0022565 Korean Patent Publication No. 10-2011-0013320

The present invention provides a triazine compound which is excellent in dispersibility and storage stability and capable of high-brightness coloring even at a high concentration.

The present invention also provides a pigment dispersion aid and a pigment surface treatment agent comprising the triazine compound of the present invention.

The present invention also provides a pigment dispersion comprising the pigment dispersion aid of the present invention.

The present invention also provides a colored photosensitive resin composition comprising the pigment dispersion of the present invention.

The present invention provides a triazine derivative useful as a dispersing aid and a pigment surface treating agent which has a high affinity with a pigment and is excellent in dispersibility so as not to affect the original spectrum of the pigment.

The triazine derivative of the present invention is represented by the following formula (1).

[Chemical Formula 1]

(In the formula 1,

X ₁ and X ₂ are independently selected from the group consisting of -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, -CH ₂ NH-, -CH ₂ - or -CH ₂ NHCOCH ₂ NH- ;

Ar ₁ is Cl, OH, a (C6-C12) aryl group or a (C3-C12) heteroaryl group;

R ₁ and R ₂ are independently of each other a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) , (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1-C5) each other Alkyl or (C6-C12) aryl group;

Z is CR ₃ or N and R ₃ is hydrogen, (C 1 -C 5) alkyl, (C 1 -C 5) alkoxy, halo (C 1 -C 5) alkyl, (C 1 -C 5) alkoxycarbonyl or An aryl group;

a is 0 or an integer of 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a and b are 2 or more, R ₁ may be different from or the same as each other;

c is 0 or an integer of 1 to 2, and when c is 2 or more, R ₂ may be the same or different from each other;

Aryl group or a heteroaryl group of said Ar ₁ group is an amino group, a halogen, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, may be substituted by (C6-C12) aryl group, at least one selected from _{SO 2 N (R 11) (} R 12) and _{-CON (R 13) (R 14} ).)

Preferably, R ₁ and R ₂ in the formula (1) according to an embodiment of the present invention are independently selected from the group consisting of a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group or (C6-C12) aryl group;

X ₁ and X ₂ are independently of each other -NH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-;

Ar ₁ is a (C6-C12) aryl group or a (C3-C12) heteroaryl group;

Z may be N.

Ar ₁ in Formula 1 according to an embodiment of the present invention may be selected from the following formulas.

(Wherein R ₂₁ to R ₂₇ are independently of each other an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) (C1-C5) alkoxycarbonyl group is, (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ), R 11 to R ₁₄ are independently of each other (C1-C5) alkyl or (C6-C12) aryl group;

D ₁ to D ₄ are independently of each other CR ₁₅ R ₁₆ or N and R ₁₅ and R ₁₆ are each independently of the other hydrogen, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) , (C1-C5) alkoxycarbonyl group or (C6-C12) aryl group;

D ₅ is CR ₁₇ or N, and, R ₁₇ is hydrogen, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, or (C6-C12 ) Aryl group;

d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, f is 0 or an integer of 1 to 4, g is 0 or an integer of 1 to 2, h is 0 or 1, And when d, e, f, g and h are integers of 2 or more, each of R ₂₁ , R ₂₂ R ₂₄ , R ₂₆ and R ₂₇ may be the same or different from each other.

Preferably, Formula 1 according to an embodiment of the present invention may be represented by Formula 2 below.

(2)

[In the formula (2)

X ₁ and X ₂ are -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, -CH ₂ NH-, -CH ₂ - or -CH ₂ NHCOCH ₂ NH-;

R ₁ is a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, (C6-C12) an aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1-C5) alkyl or (C6-C12 to each other ) Aryl group;

a is independently an integer of 0 or 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a and b are 2 or more, R ₁ may be different from or the same as each other;

,

또는

이며;Ar ₁ is

,

or

;

R ₂₁ to R ₂₂ are each independently, an amino group, a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl groups, (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1 each other -C5) alkyl or (C6-C12) aryl group;

D ₁ is CR ₁₅ R and ₁₆ or N, R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) each other An alkoxycarbonyl group or a (C6-C12) aryl group;

d is 0 or an integer of 1 to 3, e is an integer from 0 or 1 to 6, when h is an integer of 0 or 1 to 7, d, e and f is 2 or more integer, each of R _21, R _22, and And R < ₂₇ > may be the same or different from each other.

Preferably, in Formula 2 according to an embodiment of the present invention, X ₁ and X ₂ are -NH-;

R ₁ is a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, or (C6-C12) An aryl group;

a is 0 or an integer of 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a is 2 or more, R ₁ may be the same or different from each other;

,

또는

이며;Ar ₁ is

,

or

;

R ₂₁ to R ₂₂ and R ₂₇ independently represent an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) -C5) alkoxycarbonyl group or (C6-C12) aryl group;

D ₁ is N;

d is 0 or an integer of 1 to 3, e is an integer from 0 or 1 to 6, when h is an integer of 0 or 1 to 7, d, e and h is 2 or more integer, each of R _21, R _22, and And R < ₂₇ > may be the same or different from each other.

The present invention also provides a pigment dispersion auxiliary comprising the triazine derivative of the present invention.

The present invention also provides a pigment surface treatment agent comprising the triazine derivative of the present invention.

The present invention also provides a pigment dispersion comprising a pigment dispersion aid, a pigment, a pigment dispersant and a solvent.

The pigment of the pigment dispersion according to an embodiment of the present invention may have an average particle diameter of 10 to 150 nm and the pigment dispersant may be a solid content of 10 to 60 parts by weight per 100 parts by weight of the pigment, 1 to 25 parts by weight with respect to 100 parts by weight.

The present invention also provides a colored photosensitive resin composition comprising the pigment dispersion of the present invention and a photosensitive compound.

The triazine derivative of the present invention has a functional group having high affinity with the pigment, thereby effectively protecting the surface of the pigment, minimizing the damage of the pigment particles, and thus being excellent in dispersibility.

Further, the triazine derivative of the present invention can be used as a pigment surface treating agent to pigment the auxiliary pigment.

Therefore, the pigment dispersion containing the triazine derivative of the present invention is excellent in the ability to inhibit the agglomeration of the pigment and has high heat resistance and excellent storage stability.

In addition, the colored photosensitive resin composition employing the pigment dispersion of the present invention has high brightness and high color sharpness, and is excellent in dispersibility even at a high concentration, so that a low power display device can be realized.

The present invention provides a triazine derivative which is used in a pigment dispersion aid or a pigment surface treatment agent to improve dispersibility and storage stability and to stabilize a surface of a pigment to improve brightness and color sharpness of a display or the like employing the same. The triazine derivative is represented by the following formula (1).

[Chemical Formula 1]

(In the formula 1,

X ₁ and X ₂ are independently selected from the group consisting of -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, -CH ₂ NH-, -CH ₂ - or -CH ₂ NHCOCH ₂ NH- ;

Ar ₁ is Cl, OH, a (C6-C12) aryl group or a (C3-C12) heteroaryl group;

R ₁ and R ₂ are independently of each other a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) , (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1-C5) each other Alkyl or (C6-C12) aryl group;

Z is CR ₃ or N and R ₃ is hydrogen, (C 1 -C 5) alkyl, (C 1 -C 5) alkoxy, halo (C 1 -C 5) alkyl, (C 1 -C 5) alkoxycarbonyl or An aryl group;

a is 0 or an integer of 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a and b are 2 or more, R ₁ may be different from or the same as each other;

c is 0 or an integer of 1 to 2, and when c is 2 or more, R ₂ may be the same or different from each other;

Aryl group or a heteroaryl group of said Ar ₁ group is an amino group, a halogen, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, may be substituted by (C6-C12) aryl group, at least one selected from _{SO 2 N (R 11) (} R 12) and _{-CON (R 13) (R 14} ).)

The triazine derivative of the present invention has high storage stability due to its high heat resistance and remarkably improves the dispersibility by combining with various functional groups on the surface of the pigment. When applied to a pigment of a display such as a color filter employing the triazine derivative, excellent luminance and color clarity .

Specifically, the triazine derivative of the present invention can be combined with various functional groups on the surface of the pigment when used as a pigment surface treating agent by introducing a triazine derivative or a pyrimidine derivative, which is a functional group having excellent affinity with the pigment to the triazine skeleton, as a substituent, When used as a preparation, it improves the bonding force with various dispersants and dispersing resins, and improves the dispersibility remarkably.

The triazine derivative of the present invention differs from the compound of the traazine skeleton used as a conventional pigment dispersing aid in that it has high affinity with an acidic group and a pigment which can improve bonding force with a dispersing agent and a resin for dispersion, A colored photosensitive resin composition employing a pigment dispersion containing a triazine derivative or a pyrimidine derivative as a substituent to increase the dispersibility by inhibiting aggregation as a pigment dispersion auxiliary or a pigment surface treatment agent has a high brightness and a high contrast value and a low power .

More specifically, the triazine derivative of the present invention can be used as a pigment surface treating agent by introducing an acidic group, which is a substituent capable of tightly bonding with a pigment, a dispersant and a dispersing resin, or a trazine derivative or a pyrimidine derivative as a functional group, It can be easily pigmented to inhibit re-agglomeration of fine pigments. When used as a pigment dispersion aid, it can be bonded with various functional groups of the pigment to protect the surface of the pigment, and can be combined with a dispersing agent and a dispersing resin to dramatically increase the dispersibility .

Preferably, R ₁ and R ₂ in the formula (1) according to an embodiment of the present invention are independently selected from the group consisting of a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group or (C6-C12) aryl group;

X ₁ and X ₂ are independently of each other -NH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-;

Ar ₁ is a (C6-C12) aryl group or a (C3-C12) heteroaryl group;

Z may be N.

Ar ₁ in formula (1) is preferably selected from the following formulas, but is not limited thereto.

(Wherein R ₂₁ to R ₂₇ are independently of each other an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) (C1-C5) alkoxycarbonyl group is, (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ), R 11 to R ₁₄ are independently of each other (C1-C5) alkyl or (C6-C12) aryl group;

D ₁ to D ₄ are independently of each other CR ₁₅ R ₁₆ or N and R ₁₅ and R ₁₆ are each independently of the other hydrogen, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) , (C1-C5) alkoxycarbonyl group or (C6-C12) aryl group;

D ₅ is CR ₁₇ or N, and, R ₁₇ is hydrogen, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, or (C6-C12 ) Aryl group;

d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, f is 0 or an integer of 1 to 4, g is 0 or an integer of 1 to 2, h is 0 or 1, And when d, e, f, g and h are integers of 2 or more, each of R ₂₁ , R ₂₂ R ₂₄ , R ₂₆ and R ₂₇ may be the same or different from each other.

The compound of Formula 1 according to an embodiment of the present invention may be represented by the following Chemical Formula 2 in view of the dispersibility and the storage stability.

(2)

[In the formula (2)

X ₁ and X ₂ are -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, -CH ₂ NH-, -CH ₂ - or -CH ₂ NHCOCH ₂ NH-;

R ₁ is a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, (C6-C12) an aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1-C5) alkyl or (C6-C12 to each other ) Aryl group;

a is independently an integer of 0 or 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a and b are 2 or more, R ₁ may be different from or the same as each other;

,

또는

이며;Ar ₁ is

,

or

;

R ₂₁ to R ₂₂ are each independently, an amino group, a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl groups, (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1 each other -C5) alkyl or (C6-C12) aryl group;

D ₁ is CR ₁₅ R and ₁₆ or N, R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) each other An alkoxycarbonyl group or a (C6-C12) aryl group;

d is 0 or an integer of 1 to 3, e is an integer from 0 or 1 to 6, when h is an integer of 0 or 1 to 7, d, e and f is 2 or more integer, each of R _21, R _22, and And R < ₂₇ > may be the same or different from each other.

Preferably, in Formula 2 according to an embodiment of the present invention, X ₁ and X ₂ are -NH-;

R ₁ is a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, or (C6-C12) An aryl group;

a is 0 or an integer of 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a is 2 or more, R ₁ may be the same or different from each other;

,

또는

이며;Ar ₁ is

,

or

;

R ₂₁ to R ₂₂ and R ₂₇ independently represent an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) -C5) alkoxycarbonyl group or (C6-C12) aryl group;

D ₁ is N;

d is 0 or an integer of 1 to 3, e is an integer from 0 or 1 to 6, when h is an integer of 0 or 1 to 7, d, e and h is 2 or more integer, each of R _21, R _22, and R < ₂₇ > may be the same or different from each other.

Specifically, the triazine derivative of Formula 1 according to an embodiment of the present invention may be selected from the following compounds, but is not limited thereto.

,

,

The substituents comprising " alkyl ", " alkoxy " and other " alkyl " moieties described in this invention encompass both linear and branched forms.

The term "haloalkyl" in the present invention means a form in which one or more halogen atoms are substituted for an alkyl group, and examples thereof include trifluoromethane and bromomethane.

The term " aryl " in the present invention means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may be a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, A ring system, and a form in which a plurality of aryls are connected by a single bond. Specific examples include but are not limited to phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, and the like, for example, phthalimide, unsaturated indene (2H- Dione, 2,3-hydro-1H-indene), isoindoline, anthraquinone, and the like are also included in the aryl group.

"Heteroaryl" in the present invention includes 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeletal atoms and the remaining aromatic ring skeletal atoms are carbon Means a 5 to 6 membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with at least one benzene ring and may be partially saturated. The heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected to a single bond.

The triazine compounds described in the present invention are all possible methods as long as they can be recognized by those skilled in the art.

First, a sulfonic acid group is introduced by reacting a salt and cyanuric acid with a sulfonic acid compound.

In general, the amount of the sulfonic acid compound used per mole of cyanuric chloride is usually 0.5 to 1.5 mol, preferably 0.9 to 1.1 mol, and the reaction of the cyanuric chloride with the sulfonic acid compound can be carried out, for example, Stirring is carried out at -10 to 0 캜 for 1 to 2 hours, and then the reaction is terminated. The solvent may be any conventionally used solvent, for example, water, an organic solvent such as acetone, dioxane, xylene, dimethylformamide, tetrafluorfuran, or a mixture of two or more solvents.

Next, at least one compound having at least one amino group is reacted in order to introduce a substituent having a triazine group into a reaction product in which a sulfonic acid group is introduced. Specific examples of such a compound include 4-amino phthalimide and the like. The amount of the compound having at least one amino group with respect to 1 mol of the reaction product of cyanuric chloride and sulfonic acid compound is appropriately selected depending on the kind of the compound to be used but is usually from 0.5 to 2.5 mol, preferably from 0.9 to 2.0 mol have. In the reaction of introducing a basic group into the triazine skeleton into which an acidic group is introduced, organic acids such as acetic acid, benzoic acid, citric acid, fumaric acid, gluconic acid and oxalic acid, and inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid may be used as a solvent. These acids are preferably used in the form of an aqueous solution.

Finally, the reaction of introducing a triazine derivative or a pyrimidine derivative, for example, 2-amino-1,3,5-aminotriazine (2-amino-1,3,5-triazine), is stirred in an appropriate solvent or The reaction is terminated at 30 to 100 DEG C for 1 to 10 hours without stirring. As the solvent, a solvent such as a solvent used in the reaction of cyanuric chloride and a sulfonic acid compound can be used. As a result, a triazine derivative in which a different substituent is finally introduced as a basic group, an acid group and an aromatic group is finally produced. The obtained triazine derivative can be easily purified in a reaction mixture by a conventional separation and purification means such as, for example, filtration, washing and drying.

로 표시되는 유도체를 작용기로 도입하는 경우는 Pigment Red 254, 255, 264, 270, 272 및 Pigment Orange 71, 73, 81의 안료 분산 조제 및 표면처리제로 사용되는 것이 보다 바람직하다.]Preferably, the triazine derivative of the present invention is a triazine derivative having a high affinity with an acidic group and a pigment, and a functional group which is a pyrimidine derivative. In addition to the functional group, the other functional group is introduced into the parent of the pigment, It is preferable from the viewpoint of improving the acidity. For example, the triazine derivative of the present invention may contain one or more functional groups other than an acid group, a triazine derivative, and a pyrimidine derivative, such as the compounds 1a and 1b described in the present invention, when phthalimide and quinoline are introduced as functional groups, It is preferable to use phthalimide-based pigments or quinoline-based pigments having a mid and quinoline as functional groups, for example, as a pigment dispersing aid and surface treatment agent for Pigment Yellow 138. It is preferable to use anthraquinone as a functional group It is preferably used as an anthraquinone pigment, for example, as a pigment dispersing aid and surface treating agent of Pigment Red 177, 89, 83 and Pigment Violet 5: 1,

Is more preferably used as a pigment dispersing aid and surface treating agent of Pigment Red 254, 255, 264, 270, 272 and Pigment Orange 71, 73, 81. [

The present invention also provides a pigment dispersion auxiliary comprising the triazine derivative of the present invention.

The pigment dispersing aid of the present invention has high dispersibility and high storage stability by using the triazine derivative of the present invention, so that the pigment dispersion containing the same has excellent dispersibility even at a high concentration, and a colored photosensitive resin composition containing such a pigment dispersion is used A display such as a color filter has a high brightness and an excellent contrast value.

The present invention also provides a pigment surface treatment agent comprising the triazine derivative of the present invention.

The pigment surface treatment agent of the present invention can introduce a triazine derivative or a pyrimidine derivative having high affinity with a pigment as a substituent to be bonded to various functional groups of the pigment, thereby suppressing the damage of the surface of the pigment and suppressing cohesion between the prepared pigments. By incorporating the triazine derivative of the present invention, the pigment can be easily pigmented to prepare a fine pigment and inhibit re-aggregation of the fine pigment.

The present invention also provides a pigment dispersion comprising the pigment dispersing aid, pigment, pigment dispersant and solvent of the present invention.

The pigment dispersing aid used in the pigment dispersion of the present invention may be used in an amount of 1 to 25 parts by weight, preferably 1 to 10 parts by weight, based on 100 parts by weight of the pigment.

The pigment dispersion of the present invention is excellent in dispersibility and storage stability by including the pigment dispersion aid of the present invention.

The pigments contained in the pigment dispersion according to one embodiment of the present invention are not limited as long as they are organic pigments, but may be azo pigments or condensed pigments, and they may be used alone or in combination of two or more.

Specific examples of the red pigment include C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 49, 57, 60, 63, 64, 68, 69, 81, 83, 88, 101, 104, 108, 109, 112, 113, 114, 122, 123, 144, 146, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 178, 176, 177, 178, 179, 181, 184, 252, 253, 254, 255, 252, 253, 254, 252, 254, 265, 266, 267, 268, 269, 270, 272, 272, 273, 274, 275, 276, etc. Among them, CI Pigment Red, 122, 166, 168, 177, 179 202, 206, 207, 209, 224, 242, 254, 264, 269, and more preferably C.I. Pigment Red 166, 177, 179, 209, 224, 254, 264, 269, and the like.

Green pigments include C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, Preferably, the CI Pigment Green 7, 36, 58, 59, and the like.

The yellow pigments include C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 169, 170, 171, 172, 173, 193, 194, 199, 198, 213 and 214, and the like. Among these, C.I. Pigment Yellow 129, 138, 185, and the like.

The orange pigments include C.I. Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, Pigment Orange 38, 71, 73 and the like.

The pigment according to one embodiment of the present invention may have a volume average particle diameter of 10 to 150 nm, preferably 30 to 110 nm, and more preferably 40 to 80 nm.

The pigment included in the pigment dispersion of the present invention can be obtained by reacting a compound as a raw material of an organic pigment or pigmenting a pigment preparation in the presence of a pigment surface treatment agent containing the triazine derivative of the present invention.

That is, the pigment contained in the pigment dispersion of the present invention may be a fine pigment obtained by surface-treating the prepared pigment with the triazine derivative of the present invention.

The auxiliary pigment in the present invention is a compound obtained by reacting a raw material compound as a base of a condensed polycyclic pigment and having a large particle size (for example, about 10 to several hundreds of 탆). The pigment itself can be used as a pigment, And color development is not obtained. The pigments of such condensed polycyclic pigments can be prepared by known methods.

In the present invention, such a preparation pigment can be pigmented in the presence of the triazine derivative. In the present invention, the term "pigment" means a process of adjusting the particle diameter of the prepared pigment to an appropriate particle diameter range as a pigment. The suitable particle size also varies depending on the application and the like, but it may be 0.05 to 0.3 탆.

As the method of pigmentation, a known method such as salt milling can be used. The amount of the triazine derivative to be added in pigmenting is not particularly limited, but may be added in an amount of 0.1 to 20 parts by weight of the triazine derivative per 100 parts by weight of the pigment to be prepared. If the added amount of the triazine derivative is less than 0.1 part by weight, the crystal growth inhibiting effect is small. If the added amount is more than 20 parts by weight, the transparency and contrast of the final product may be affected.

The pigments are pigmented, washed with water by a conventional method, dried and then pulverized by a disperser such as a roll mill or a bead mill to obtain a fine pigment composition comprising a condensed polycyclic pigment having a very fine particle size and a very small primary particle size.

The triazine derivative of the present invention obtained as described above and the fine pigment composition containing the desired organic pigment are obtained by a method in which the desired organic pigment is highly refined and, for example, the primary particle of the organic pigment has a long diameter of 50 to 150 nm , And has a short diameter of 30 to 100 nm.

In addition, the fine pigment composition prepared as described above has a very small primary particle size of the organic pigment and can be highly refined and at the same time can remarkably suppress cohesion. Even when dispersed in a pigment dispersion, Can be effectively prevented, and can be easily applied to a colored photosensitive resin composition for a color filter having high brightness and excellent contrast value.

The pigment dispersant according to one embodiment of the present invention is typically used for preparing a colored photosensitive resin composition for a color filter. For example, it is suitable to include an amine group or an ammonium salt group as a pigment-affinity group, Polyurethane, polyethylene imine, and mixtures thereof. Commercially available dispersing agents include Disperbyk-160, Disperbyk-161, Disperbyk-165, Disperbyk-168, Disperbyk-170, Disperbyk-171, Disperbyk- 2000, Disperby-2001; Disperhib-Lin2 1116; LPN-22484, LPN-22484, LPN-22421, LPN-22470, LPN-22558, LPN-22822, LPN-22964, LPN-22481, LPN- LPN-22474, LPN-22480, LPN-22478, LPN-22475, LPN-23170, LPN-23171, LPN-23172; EFKA-4046, EFKA-4047 and EFKA-4340 from EFKA; Solsperse -5000, Sol Spurs-12000, Sol Spurs-22000, Sol Spurs-24000, and Sol Spurs-32500 from AVECIA; And PB-821, PB-822, PB-824 and PB-827 of Ajinomoto Co., These dispersants may be used alone or in combination of two or more.

The pigment dispersant according to one embodiment of the present invention is a pigment dispersant based on the solid content of the pigment dispersant in terms of storage stability and a problem that the development speed of an alkali developing solution is slowed down when a photosensitive resin containing a pigment dispersion is produced, 10 to 80 parts by weight, preferably 10 to 60 parts by weight, and more preferably 20 to 50 parts by weight, based on 100 parts by weight of the resin composition.

The pigment dispersion according to an embodiment of the present invention may further include an alkali-soluble resin as a dispersing resin, and is typically used in a colored photosensitive resin composition for a color filter, and may be an acrylic polymer Resins are preferred.

Specific examples of monomers usable in the acrylic resin include compounds having at least one carboxyl group in the molecule (e.g., acrylic acid, methacrylic acid, maleic acid, and fumaric acid); Aromatic vinyl compounds such as styrene,? -Methylstyrene, vinyltoluene, vinylbenzylmethylether, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate and the like; Unsaturated carboxylate compounds (e.g., methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate); Compounds having a hydroxyl group (e.g., 2-hydroxyalkyl (meth) acrylate, glycerol (meth) acrylate); (Meth) acrylamide, secondary or tertiary Aactyl acrylamide, dialkylaminoalkyl (meth) acrylate, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, Vinyltriazole); Branched or straight chain butyl (meth) acrylate, ethylhexyl (meth) acrylate, phenoxyhydroxypropyl (meth) acrylate; Other examples of the hydrophilic compound include monomers containing a tetrahydrofurfuryl group, a phosphoric acid moiety, a phosphoric acid ester moiety, a quaternary ammonium salt moiety, an ethyleneoxy chain, a propyleneoxy chain, and a sulfonic acid group.

In order to increase the crosslinking efficiency, the resin may have a polymerizable group in the side chain.

The acrylic resin preferably has a weight average molecular weight (measured by GPC method, in terms of polystyrene) of 1,000 to 200,000, more preferably 2,000 to 50,000.

The dispersible resin may be used in an amount of 10 to 80 parts by weight, preferably 10 to 60 parts by weight, more preferably 20 to 50 parts by weight, based on 100 parts by weight of the pigment of the present invention.

The solvent used in the pigment dispersion according to one embodiment of the present invention may be any of various known solvents without any particular limitation. Specific examples thereof include alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; , Ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone, gamma-butyrolactone, ethyl lactate, butyl lactate and ethyl pyruvate. These solvents may be used alone or in combination of two or more.

The solvent may be used in an amount of preferably 70 to 90% by weight, more preferably 75 to 85% by weight, based on the total weight of the pigment dispersion.

The pigment dispersion according to an embodiment of the present invention may further include a conventional surfactant or an organic acid as an additive in order to improve the dispersion stability of the pigment, thermal stability and alkali development.

As the surfactant used in the pigment dispersion according to one embodiment of the present invention, various surfactants known in the art can be used without any particular limitation. Commercially available surfactants include Megafac R08 and Megafac F477 Manufactured by Ink & Chemicals Corporation).

Since the pigment dispersion of the present invention contains the triazine derivative of the present invention, storage stability and dispersibility are high, and the brightness and contrast ratio characteristics of a display such as a color filter using the colored photosensitive resin composition employing it are remarkably improved.

The present invention also provides a colored photosensitive resin composition comprising the pigment dispersion of the present invention and a photosensitive compound.

The photosensitive compound of the present invention may be usually a colorant, and the colorant may be a pigment, a dye, or a mixture thereof.

As the pigment, the above-mentioned pigments can be used. As the dyes, dyes conventionally used as colorants are all possible. Specific examples thereof include acid yellow 1, 3, 5, 7, 11, 17, 23 , 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 134 , 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204 , 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; Solvent yellow 14, 23, 38, 62, 63, 64, 68, 78, 82, 89, 90, 91, 92, 94, 98, 99, 104, 105, 106, 126, 128, 129, 130, 132, 133, 134, 138, 139, 140, 144, 145, 156, 160, 161, 162, 163, 164, 165, 168, 169, 170, 171; Acid red 29, 31, 51, 52, 92, 94, 97, 133, 134, 158, 176, 183, 198, 249, 266, 289, 308; Acid orange 6, 7, 8, 10, 12, 26, 51, 52, 62, 63, 64, 74, 107, 169 and the like.

The colored photosensitive resin composition according to an embodiment of the present invention may further include a photoinitiator and a crosslinking agent. Various photoinitiator compounds known in the art may be used without limitation, as the photoinitiator used in the present invention. Specific examples thereof include iodine salt compounds, sulfonium salt compounds, organic halogen compounds, oxime compounds, and mixtures thereof. Commercially available photoinitiators include Ciba Geigy's Irgacure-907, Irgacure-369, Irgacure OXE 01, Irgacure OXE 02, and the like. The photoinitiator may be used in an amount of preferably 0.1 to 5% by weight based on the total weight of the colored photosensitive resin composition. Each photoinitiator may be used alone or in combination of two or more. As the crosslinking agent used in the present invention, various known crosslinking compound may be used without particular limitation. Specific examples thereof include ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate having 2 to 14 ethylene groups, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) Pentaerythritol tetra (meth) acrylate, 2-trisacryloyloxymethylethylphthalic acid, propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate having 2 to 14 propylene groups (Meth) acrylate, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate. These crosslinking agents may be used alone or in combination of two or more. The crosslinking agent may be used in an amount of preferably 0.5 to 10% by weight based on the total weight of the colored photosensitive resin composition.

The colored photosensitive resin composition employing the pigment dispersion containing the triazine derivative of the present invention has excellent transparency and tinting power, and therefore can be very usefully used in the production of a low power color reproduction color filter.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention and are not intended to limit the scope of the present invention.

[Example 1] Preparation of Compound 1a

Cyanuric chloride (9.3) g was dissolved in acetone (500 mL). Sulfanilic acid (8.6 g), which reacts with one chlorine atom of cyanuric chloride, was added and reacted at 0 ° C for 1 hour. Here, 8.1 g of 4-amino phthalimide was added and reacted at 40 占 폚 for 1 hour. Then, an additional (8.1) g of 2-aminotriazine (2-amino-1,3,5-triazine) was added and reacted at 90 ° C for 5 hours. The resulting reaction product was leached, washed with water, and then allowed to stand in a thermostatic chamber at 100 ° C overnight to be dried to obtain the desired compound 1a (18.9 g). (LC / MS, m / z = 506)

[Example 2] Preparation of compound 1b

Compound 1b and (18.2) g were obtained in the same manner as in Example 1 except that 8-aminoquinoline (7.2 g) was used instead of 4-aminophthalimide in Example 1. (LC / MS, m / z = 488)

[Example 3] Preparation of Compound 1c

Compound 1c (19.3) was obtained in the same manner as in Example 1 except that 2-aminoanthraquinone (11.2 g) was used instead of 4-aminophthalimide in Example 1. (LC / MS, m / z = 567)

[Examples 4 to 5] Preparation of pigment dispersion

The ingredients shown in the following Table 1 and the amount of the ingredients shown in Table 1 were put into a mixer having an inner volume of 1000 mL and 360 g of zirconia beads having a diameter of 1.0 mm were placed in a disper and stirred at 200 rpm for 60 minutes to prepare a preliminary dispersion Respectively.

ingredient Usage (g) C.I. Pigment Yellow 138 40.00 g The triazine compound 1a of the present invention 1.20 g Pigment dispersant (trade name: BYK LPN-22102, solid content concentration 38.7%) 31.01 g Dispersible resin (trade name: Showa 19X, solid content concentration 27.9%) 71.68 g PGMEA (propylene glycol monomethyl ether acetate) 96.11 g

400 g of zirconia beads (0.1 mm in diameter) having a diameter of 0.1 mm were stirred for 10 hours at 200 rpm for 10 hours to obtain 200 g of the preliminary dispersion obtained by filtering the preliminary dispersion with 325 SUS MESH. 100 g of PGMEA was added to the resultant dispersion, and the mixture was further stirred at 200 rpm for 10 minutes. The resulting final dispersion was filtered with a 0.45 μm PP filter (Whatman 0.45 PP Filter, Whatman) to obtain a yellow pigment dispersion.

Similarly, a pigment dispersion was prepared in the same manner as above except that the triazine compound 1b prepared in Example 2 of the present invention was used instead of the triazine compound 1a.

[Example 6] Production of pigment dispersion

In Example 4, C.I. Instead of Pigment Yellow 138, C.I. A pigment dispersion was prepared in the same manner as in Example 4, except that Pigment Red 177 was used and 1c was used instead of the triazine compound 1a.

[Comparative Examples 1 and 2] Preparation of Comparative Pigment Dispersion

A pigment dispersion was prepared in the same manner as in Example 4, except that the following Comparative Compound 1 or the following Comparative Compound 2 was used instead of the triazine compound prepared in Example 1 of the present invention in Example 4 to prepare a pigment dispersion .

Comparative Compound 1 was prepared as follows.

A 500 mL four-necked flask was charged with 450 g of 101% sulfuric acid prepared from 25% fuming sulfuric acid and sulfuric acid. Pigment Yellow 138, 45 g was added in small portions. The mixture was stirred at 80 DEG C for 3 hours, and the reaction solution was stirred in 5000 parts of ice water to precipitate the sulfonated product. The precipitated sulfonate was separated by filtration, washed with 2 L of 0.1% hydrochloric acid, and further washed with 2 L of purified water to obtain a sulfonated product (43 g) of the pigment.

Elemental analysis (C27H7Cl8NO7S) Calculated: C 41.95; H 0.91; Cl 36.69; N 1.81; 0 14.49; S 4.15; Measured: C 41.90; H 0.96; Cl 36.63; N 1.74; Lt; / RTI > S 4.06

The following Comparative Compound 2 was prepared in the same manner as described in Korean Patent Publication No. 2011-0013320 as follows.

Cyanuric chloride (9.3 g) was dissolved in 500 mL of acetone, and a sulfanilic acid (8.6 g), which reacted with one chlorine atom of cyanuric chloride, was added thereto, followed by reaction at 0 ° C for 1 hour. 4,4'-methylenebis (2,6-dimethylaniline) (15.8 g) was added thereto, and the reaction was allowed to proceed at 40 ° C. for 1 hour. The resulting residue was washed with water and then allowed to stand in a thermostatic chamber at 100 ° C overnight to be dried to obtain the target triazine compound 1 (23.5 g).

[Comparative Examples 3 to 4] Preparation of comparative pigment dispersions

In Comparative Examples 1 and 2, C.I. Instead of Pigment Green 58, C.I. Except that Pigment Red 254 was used instead of Pigment Red 254 to prepare a red pigment dispersion.

[Examples 7 to 8] Preparation of colored photosensitive resin composition

Preparation of Green Pigment Dispersion

The components and the contents shown in Table 2 were placed in a mixer having an inner volume of 1000 mL and 360 g of zirconia beads having a diameter of 1.0 mm were placed and dispersed by a disperser at 200 rpm for 60 minutes to prepare a preliminary dispersion Respectively.

400 g of zirconia beads (0.1 mm in diameter) having a diameter of 0.1 mm were stirred for 10 hours at 200 rpm for 10 hours to obtain 200 g of the preliminary dispersion obtained by filtering the preliminary dispersion with 325 SUS MESH. 100 g of PGMEA was added to the resultant dispersion, and the mixture was further stirred at 200 rpm for 10 minutes. The resulting final dispersion was filtered with a 0.45 μm PP filter (Whatman 0.45 PP Filter, Whatman) to obtain a green pigment dispersion.

ingredient Usage (g) C.I. Pigment Green 58 40.00 g Pigment dispersant (trade name: BYK LPN-22251, solid content concentration: 41.2%) 29.13 g Dispersible resin (trade name: Showa 19X, solid concentration 27.9%) 71.68 g PGMEA (propylene glycol monomethyl ether acetate) 97.99g

Each of the yellow pigment dispersions obtained in Example 4 was mixed with the green pigment dispersion obtained above in a ratio of 4: 6 (weight ratio) to prepare respective colored photosensitive resin compositions. The resulting colored photosensitive resin compositions were applied to respective films And dried on a hot plate at 100 ° C for 10 minutes to obtain a coating film. The obtained coated film was exposed to light with an amount of 100 mJ / cm ² using an ultra-high pressure mercury lamp, developed with an alkaline developer, and then rinsed with ultrapure water. The developed coating film was thermally cured in an oven at 230 캜 for 20 minutes to form a pattern for a color filter. The chromaticity (x, y, Y) of the thermosetting coating film was measured using a colorimeter MCPD-3000 (manufactured by Ohtsuka), and the results are shown in Table 3 below.

[Comparative Examples 5 and 6] Preparation of colored photosensitive resin composition

Colored photosensitive resin compositions were prepared in the same manner as in Examples 7 to 8 except that the pigment dispersions of Comparative Examples 1 and 2 were used instead of the Example 4 and Example 5 in Examples 7 to 8, A pattern for a color filter was formed in the same manner. The chromaticity (x, y, Y) of the thermosetting coating film was measured using a colorimeter MCPD-3000 (manufactured by Ohtsuka), and the results are shown in Table 3 below.

Colored photosensitive resin composition The triazine compound used in the pigment dispersion Y x y CR (%) Submerged water
(Lv. 1-5) Example 7 1a 61.74 0.2738 0.57 111% One Example 8 1b 61.69 0.2737 0.57 107% One Comparative Example 5 Comparative compound 1 60.48 0.2733 0.57 100% 5 Comparative Example 6 Comparative compound 2 60.54 0.2735 0.57 99% 2

[Examples 9 to 7 to 8] Preparation of colored photosensitive resin composition

Preparation of Red Pigment Dispersion

In Examples 7 to 8, C.I. Instead of Pigment Green 58, C.I. Except that Pigment Red 254 was used instead of Pigment Red 254. The red pigment dispersion was prepared in the same manner as in Examples 7 to 8 except that Pigment Red 254 was used.

In Examples 7 to 8, the same procedure as in Examples 7 to 8 was carried out except that the pigment dispersion prepared in Example 6 was used in place of the pigment dispersion prepared in Examples 4 to 5 and the red pigment dispersion prepared above was used To prepare a colored photosensitive resin composition, and a pattern for a color filter was formed in the same manner as in Examples 7 to 8. The chromaticity (x, y, Y) of the thermosetting coating film was measured using a colorimeter MCPD-3000 (manufactured by Ohtsuka) and the results are shown in Table 4 below.

[Comparative Examples 7 to 8] Preparation of colored photosensitive resin composition

The procedure of Example 9 was repeated except that the pigment dispersions prepared in Comparative Examples 3 to 4 and the red pigment dispersions prepared in Example 9 were used instead of the pigment dispersions prepared in Example 6, To prepare a photosensitive resin composition.

The chromaticity (x, y, Y) of the thermally cured coating film was measured using a colorimeter MCPD-3000 (manufactured by Ohtsuka Co., Ltd.) by forming a pattern for a color filter in the same manner as in Example 9, Respectively.

Colored photosensitive resin composition The triazine compound used in the pigment dispersion Y y x CR (%) Submerged water
(Lv. 1-5) Example 9 4c 16.95 0.3158 0.655 101% One Comparative Example 7 Comparative compound 1 16.77 0.3156 0.655 100% 3 Comparative Example 8 Comparative compound 2 16.80 0.3156 0.655 99% 2

As shown in Tables 3 and 4, when the colored photosensitive resin composition using the pigment dispersion containing the triazine derivative of the present invention had excellent Y value (transmittance) as compared with the colored photosensitive resin composition using the pigment dispersion containing the compound of the comparative example, , And it was confirmed that it has a superior relative luminance value.

Claims (11)

A triazine derivative represented by the following formula (1).
[Chemical Formula 1]

(In the formula 1,
X ₁ and X ₂ are independently selected from the group consisting of -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, -CH ₂ NH-, -CH ₂ - or -CH ₂ NHCOCH ₂ NH- ;
Ar ₁ is Cl, OH, a (C6-C12) aryl group or a (C3-C12) heteroaryl group;
R ₁ and R ₂ are independently of each other a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) , (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1-C5) each other Alkyl or (C6-C12) aryl group;
Z is CR ₃ or N and R ₃ is hydrogen, (C 1 -C 5) alkyl, (C 1 -C 5) alkoxy, halo (C 1 -C 5) alkyl, (C 1 -C 5) alkoxycarbonyl or An aryl group;
a is 0 or an integer of 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a and b are 2 or more, R ₁ may be different from or the same as each other;
c is 0 or an integer of 1 to 2, and when c is 2 or more, R ₂ may be the same or different from each other;
Aryl group or a heteroaryl group of said Ar ₁ group is an amino group, a halogen, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, may be substituted by (C6-C12) aryl group, at least one selected from _{SO 2 N (R 11) (} R 12) and _{-CON (R 13) (R 14} ).) The method according to claim 1,
In Formula 1, R ₁ and R ₂ are independently from each other are selected from halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1- C5) alkoxycarbonyl group or (C6-C12) aryl group;
X ₁ and X ₂ are independently of each other -NH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-;
Ar ₁ is a (C6-C12) aryl group or a (C3-C12) heteroaryl group;
And Z is N. The method according to claim 1,
The triazine derivative in the formula 1 is Ar ₁ is selected from the following structural formulas.

(Wherein R ₂₁ to R ₂₇ are independently of each other an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) (C1-C5) alkoxycarbonyl group is, (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ), R 11 to R ₁₄ are independently of each other (C1-C5) alkyl or (C6-C12) aryl group;
D ₁ to D ₄ are independently of each other CR ₁₅ R ₁₆ or N and R ₁₅ and R ₁₆ are each independently of the other hydrogen, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) , (C1-C5) alkoxycarbonyl group or (C6-C12) aryl group;
D ₅ is CR ₁₇ or N, and, R ₁₇ is hydrogen, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, or (C6-C12 ) Aryl group;
d is 0 or an integer of 1 to 3, e is 0 or an integer of 1 to 6, f is 0 or an integer of 1 to 4, g is 0 or an integer of 1 to 2, h is 0 or 1, And when d, e, f, g and h are integers of 2 or more, each of R ₂₁ , R ₂₂ R ₂₄ , R ₂₆ and R ₂₇ may be the same or different from each other. The method according to claim 1,
Wherein said formula (1) is a triazine derivative represented by the following formula (2).
(2)

[In the formula (2)
X ₁ and X ₂ are -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, -CH ₂ NH-, -CH ₂ - or -CH ₂ NHCOCH ₂ NH-;
R ₁ is a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, (C6-C12) an aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1-C5) alkyl or (C6-C12 to each other ) Aryl group;
a is independently an integer of 0 or 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a and b are 2 or more, R ₁ may be different from or the same as each other;
Ar ₁ is

,

or

;
R ₂₁ to R ₂₂ are each independently, an amino group, a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl groups, (C6-C12) aryl _{group, -SO 2 N (R 11)} (R 12) or _{-CON (R 13) (R 14} ) , and, R ₁₁ to R ₁₄ are independently hydrogen, (C1 each other -C5) alkyl or (C6-C12) aryl group;
D ₁ is CR ₁₅ R and ₁₆ or N, R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) each other An alkoxycarbonyl group or a (C6-C12) aryl group;
d is 0 or an integer of 1 to 3, e is an integer from 0 or 1 to 6, when h is an integer of 0 or 1 to 7, d, e and f is 2 or more integer, each of R _21, R _22, and And R < ₂₇ > may be the same or different from each other. 5. The method of claim 4,
Wherein X ₁ and X ₂ are -NH-;
R ₁ is a halogen group, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl, (C1-C5) alkoxycarbonyl group, or (C6-C12) An aryl group;
a is 0 or an integer of 1 to 5, b is an integer of 1 to 5, a + b? 5, and when a is 2 or more, R ₁ may be the same or different from each other;
Ar ₁ is

,

or

;
R ₂₁ to R ₂₂ and R ₂₇ independently represent an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxy group, a halo (C 1 -C 5) -C5) alkoxycarbonyl group or (C6-C12) aryl group;
D ₁ is N;
d is 0 or an integer of 1 to 3, e is an integer from 0 or 1 to 6, when h is an integer of 0 or 1 to 7, d, e and h is 2 or more integer, each of R _21, R _22, and And R < ₂₇ > may be the same or different from each other. A pigment dispersing aid comprising a triazine derivative of any one of claims 1 to 5. A pigment surface treatment agent comprising a triazine derivative according to any one of claims 1 to 5. A pigment dispersion comprising the pigment dispersion auxiliary, pigment, pigment dispersant and solvent according to claim 6. 9. The method of claim 8,
Wherein the pigment has a volume average particle diameter of 10 to 150 nm. 9. The method of claim 8,
Wherein the pigment dispersant is in a solid content of 10 to 60 parts by weight based on 100 parts by weight of the pigment, and the pigment dispersion aid comprises 1 to 25 parts by weight based on 100 parts by weight of the pigment. A colored photosensitive resin composition comprising a pigment dispersion according to any one of claims 8 to 10.