KR20170129400A - triazine derivatives with high pigment affinity, 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 dispersing aid containing the same, and a pigment dispersion containing the same, wherein the triazine derivative of the present invention has excellent dispersibility so as to improve the dispersibility and storage stability of a pigment dispersion containing the triazine derivative. Therefore, a colored photosensitive resin composition employing the pigment dispersion of the present invention has excellent optical properties.

Description

[0001] The present invention relates to a triazine derivative having high affinity with a pigment, a pigment dispersion preparation containing the same, and a pigment dispersion containing the triazine derivative with a high pigment affinity,

The present invention relates to a triazine derivative, a pigment dispersion aid comprising the same, and more particularly to a pigment dispersion and a pigment dispersion containing a triazine derivative, a pigment dispersion aid, a pigment dispersion aid, The present invention relates to a colored photosensitive resin composition.

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 pigment dispersing aid which is added to a pigment dispersion to improve storage stability and dispersibility, or a triazine compound which can be used as a pigment surface treating agent.

The present invention also provides a pigment dispersion preparation 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 treatment agent having high heat resistance and excellent storage stability without affecting the original spectrum of the pigment, and the triazine derivative of the present invention is represented by the following formula (1).

[Chemical Formula 1]

(In the formula 1,

X ₁ to X ₂ are each 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 a (C6-C12) aryl group or a (C3-C12) heteroaryl group;

,

,

또는

이며,Z is Cl, OH,

,

,

or

Lt;

R ₁ to R ₅ 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 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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;

R is 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) alkoxy group, a halo (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxycarbonyl group, C12) _{aryl, -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 to each other -C12) 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 may be different from or the same as each other;

The aryl or heteroaryl group of Ar ₁ may be substituted with at least one substituent 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) alkoxy group, a halo (C 1 -C 5) 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} ).)

In one embodiment of the present invention, X ₁ and X ₂ are independently selected from the group consisting of -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH-, and -CH ₂ NH -;

Ar ₁ And Z may be the same as each other.

(Wherein R ₁ to R ₅ 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) 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 each independently Hydrogen, (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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other.)

Preferably, Formula 1 according to an embodiment of the present invention may be represented by the following Formulas 2 to 3.

(2)

(3)

(In the above formulas 2 and 3,

X ₁ to X ₂ are each 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- ;

,

,

또는

이며,Z is Cl, OH,

,

,

or

Lt;

R ₁ to R ₅ 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 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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;

R is 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) alkoxy group, a halo (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxycarbonyl group, C12) _{aryl, -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 to each other -C12) 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, Rs may be different from or the same as each other.

Preferably, X ₁ to X ₂ in the general formulas (2) and (3) according to an embodiment of the present invention are -NH-;

또는

이며,Z is Cl, OH,

or

Lt;

R ₁ to R ₂ are, each independently, 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 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 N;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;

R is independently selected from the group consisting of a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1- C12) aryl group.

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 is useful as a pigment dispersing aid or as a pigment surface treating agent to effectively protect the surface of a pigment to minimize damage of the pigment particles and to provide a display device (display) employing a pigment dispersion containing the triazine derivative of the present invention, Can produce high brightness.

Further, the triazine derivative of the present invention is excellent in heat resistance, so that the storage stability of the pigment dispersion containing the same is excellent, and the ability to inhibit aggregation of the pigment is excellent, and the coloring brightness of the colored photosensitive resin composition employing the pigment dispersion is remarkable .

Further, the triazine compound of the present invention can be used as a surface treating agent for pigments, and the prepared pigment can be finely pigmented, and the produced fine pigment inhibits re-aggregation, thereby enhancing the dispersibility of the pigment dispersion containing the pigments.

In addition, the pigment dispersion containing the pigment dispersing aid of the present invention has high storage stability and excellent dispersibility, so that the colored photosensitive resin composition employing the pigment dispersion has a high brightness and high color sharpness and is excellent in dispersibility even at a high concentration, It is possible.

The present invention provides a triazine derivative which is used as a pigment dispersing aid or a pigment surface treating agent to improve dispersibility and storage stability and to stabilize a surface of a pigment to improve the brightness and color clarity of a display employing the same. The azine derivative is represented by the following formula (1).

[Chemical Formula 1]

(In the formula 1,

X ₁ to X ₂ are each 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 a (C6-C12) aryl group or a (C3-C12) heteroaryl group;

,

,

또는

이며,Z is Cl, OH,

,

,

or

Lt;

R ₁ to R ₅ 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 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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;

R is 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) alkoxy group, a halo (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxycarbonyl group, C12) _{aryl, -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 to each other -C12) 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 may be different from or the same as each other;

The aryl or heteroaryl group of Ar ₁ may be substituted with at least one substituent 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) alkoxy group, a halo (C 1 -C 5) 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 heat resistance when used as a pigment dispersing aid and a pigment surface treating agent and has a high storage stability and remarkably improves dispersibility by combining with various functional groups on the surface of a pigment, It has excellent brightness and color sharpness.

Specifically, the triazine derivative of the present invention can be prepared by introducing a triazine skeleton having an acid group and a specific substituent which is not a substituent of a pigment, a starting material or an intermediate in the preparation of the pigment, When used as a pigment dispersing aid, it is possible to improve the dispersibility by improving bonding force with various dispersing agents and dispersing resins and the like.

Unlike the compounds of the traazine skeleton used as the conventional pigment dispersing aid, the triazine derivatives of the present invention introduce an acid group capable of improving the binding force with the dispersing agent, the dispersing resin and the like in the triazine skeleton, A pigment dispersion containing the triazine derivative of the present invention by introducing a specific functional group (Z in the formula 1 of the present invention, specifically a phthalimide derivative, a quinoline derivative, etc.) having a similar structure of the parent or pigment matrix of the present invention, The stability is remarkably improved and the colored photosensitive resin composition employing it has high brightness, high contrast value and low power.

Further, the triazine derivative of the present invention is a pigment surface treating agent by introducing a specific functional group, which is a functional group capable of endowing with a pigment, a dispersant, a dispersing resin and the like and capable of enhancing affinity with the pigment, When used as a pigment dispersing aid, it can be combined with various functional groups of the pigment to protect the surface of the pigment, and can be combined with a dispersant, a dispersing resin and the like to dramatically improve the dispersibility.

X ₁ and X ₂ in the formula 1 according to an embodiment of the present invention are independently selected from the group consisting of -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-; Ar ₁ And Z may be the same as each other.

(Wherein R ₁ to R ₅ 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) 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 each independently Hydrogen, (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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other.)

More preferably, X ₁ and X ₂ in the general formula (1) according to an embodiment of the present invention are independently -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-; Z is Cl or OH; Ar ₁ Can be selected from the following structures.

(In the above structural formula, R ₁ to R _5, independently of each other, an amino group, a halogen, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl group, (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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ 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 Formulas 2 to 3, in view of the dispersibility and the storage stability.

(2)

(3)

(In the above formulas 2 and 3,

X ₁ to X ₂ are each 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- ;

,

,

또는

이며,Z is Cl, OH,

,

,

or

Lt;

R ₁ to R ₅ 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 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;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;

R is 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) alkoxy group, a halo (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxycarbonyl group, C12) _{aryl, -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 to each other -C12) 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, Rs may be different from or the same as each other.

Preferably, X ₁ to X ₂ in the general formulas (2) and (3) according to an embodiment of the present invention are -NH-;

또는

이며,Z is Cl, OH,

or

Lt;

R ₁ to R ₂ are, each independently, 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 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 N;

c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;

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 may be different from or the same as each other;

R is independently selected from the group consisting of a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1- C12) aryl group.

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.

In the above formula (1) according to an embodiment of the present invention, Cl (OH) means that the main product contains Cl or OH as a by-product. In a specific embodiment, it is very difficult to separate these two compounds. RTI ID = 0.0 > OH. ≪ / RTI >

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 "aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and is a single or fused ring containing 6 to 20 ring atoms, preferably 6 or 12 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, including phthalimide, unsaturated indene (2H- 1,3-dione, 2,3-hydro-1H-indene), isoindoline 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.

&Quot; Alkenyl " as used in this invention means a straight or branched chain hydrocarbon radical containing 2 to 5 carbon atoms and at least one carbon to carbon double 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 to be used per mol of cyanuric chloride may be 0.5 to 1.5 mol, preferably 0.9 to 1.1 mol, and the reaction of the cyanuric chloride and the sulfonic acid compound may be carried out, for example, After stirring at -10 to 0 캜 for 1 to 2 hours without stirring, 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 the reactant into which the sulfonic acid group has been introduced, in order to introduce the parent of the pigment, a starting material for preparing the pigment, or a specific functional group which is an intermediate. Specific examples of such a compound include 4-aminophthalimide and the like. The amount of the compound having at least one amino group based on 1 mol of the reaction product of cyanuric chloride and the sulfonic acid compound is appropriately selected depending on the kind of the compound used, but may be 0.5 to 2.0 mol, preferably 0.9 to 1.5 mol . In the reaction for introducing such a functional group into the triazine skeleton introduced with an acidic group, an organic acid such as acetic acid, benzoic acid, citric acid, fumaric acid, gluconic acid or oxalic acid, or an inorganic acid such as hydrochloric acid, sulfuric acid or nitric acid may be used as a solvent. These acids are preferably used in the form of an aqueous solution.

The reaction is terminated at 30 to 100 DEG C for 1 to 10 hours without stirring or stirring in an appropriate solvent. As the solvent, a solvent such as a solvent used in the reaction of cyanuric chloride and a sulfonic acid compound can be used. A specific functional group having an amino group in addition to an acid group and a triazine skeleton into which a specific functional group is introduced may be further reacted to produce triazine having an acidic group and two different or the same specific functional groups. As a result, a triazine derivative into which a functional group, which is a starting material or an intermediate of a pigment, as a starting material or a pigment, 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 preferably used in order to improve the dispersibility by introducing an acid group and a parent substance of a high affinity with the pigment, a starting material or an intermediate in the production of the pigment. For example, the triazine derivatives of the present invention can be prepared by reacting phthalimides and quinolines such as the compounds 1a, 1, 2a and 2b according to the invention, which are acidic groups and the parent of the pigment, Is preferably used as a phthalimide-based pigment and a quinoline-based pigment having phthalimide and quinoline, for example, as a pigment dispersing aid and surface-treating agent for Pigment Yellow 138,

It is more preferable to use a derivative represented by the following formula 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, and thus the pigment dispersion containing the pigment dispersion has high dispersibility, and a pigment dispersing aid prepared using the colored photosensitive resin composition containing such a pigment dispersion 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 includes the triazine derivative of the present invention which has a remarkable effect of being able to bond with various functional groups of the pigment to suppress damage to the surface of the pigment and inhibit aggregation between the pigment preparations, Fine pigment can be produced.

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 addition amount of the triazine derivative at the time of pigmentation is not particularly limited, but it may be added in an amount of 0.1 to 20 parts by weight of the triazine precursor to 100 parts by weight of the prepared pigment. 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 characterized in that the desired organic pigment is highly finely dispersed, and for example, as a primary particle of the organic pigment, the long diameter is 50 to 150 nm, And a short diameter of 30 to 100 nm can be obtained.

In addition, the fine pigment composition prepared as described above has a very small primary particle size of the organic pigment, can be highly refined and can significantly inhibit cohesiveness. Even when dispersed in a pigment dispersion, the coagulation can be effectively And can be easily applied to a colored photosensitive resin composition for a color filter having a high brightness and an 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] Production of triazine derivative 1a

Cyanuric chloride (9.3 g) was dissolved in acetone (500 mL), and then added with sulfanilic acid (8.6 g), which reacted with one chlorine atom of cyanuric chloride, and reacted at 0 ° C for 1 hour. 4-Aminophthalimide (8.1 g) was added thereto and reacted at 40 占 폚 for 1 hour. Then, 4-amino phthalimide (8.1 g) was further added thereto and reacted at 90 DEG 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 20.2 g of the desired triazine compound 1a. (LC / MS, m / z = 572)

[Example 2] Preparation of triazine derivative 1b

(20.07) g was obtained in the same manner as in Example 1, except that the step of addition of 4-aminophthalimide in Example 1 was not carried out. (LC / MS, m / z = 446)

[Example 3] Production of triazine derivative 2a

(19.1) g was obtained in the same manner as in Example 1 except that 8-aminoquinoline (7.2 g) was added instead of 4-aminophthalimide in Example 1 . (LC / MS, m / z = 536)

[Example 4] Production of triazine derivative 2b

Compound 2b (18.7) g was obtained in the same manner as in Example 3, except that the reaction was carried out without adding the additional 8-aminoquinoline in Example 3. (LC / MS, m / z = 428)

[Examples 5 to 8] 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, the pigment dispersions were prepared in the same manner as in Example 5, except that the triazine compounds 1b, 2a and 2b prepared in Examples 2 to 4 of the present invention were respectively used instead of the triazine compound 1a.

[Comparative Examples 1 and 2]

A pigment dispersion was prepared in the same manner as in Example 4, except that the triazine compound prepared in Example 1 of the present invention was replaced with the following Comparative Example Compound 1 or the following Comparative Compound 2, To prepare a 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 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, allowed to stand in a constant temperature oven at 100 ° C overnight, and dried to obtain the objective compound (2) (23.5 g).

[Examples 9 to 12 and Comparative Examples 3 to 4] 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 A resinous dispersant (trade name: BYK LPN-22251, solid concentration: 41.2%) 29.13 g Resin type dispersant (trade name: Showa 19X, solid content concentration 27.9%) 71.68 g PGMEA (propylene glycol monomethyl ether acetate) 97.99g

The yellow pigment dispersions obtained in Examples 5 to 8 were mixed with the green pigment dispersion obtained above in a ratio of 4: 6 (weight ratio) to prepare respective colored photosensitive resin compositions. The colored photosensitive resin compositions thus obtained were subjected to spin coating 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.

Colored photosensitive resin composition Triazine derivatives used in pigment dispersions Y x y CR (%) Submerged water
(Lv. 1-5) Example 9 1a 60.72 0.2735 0.57 105% One Example 10 1b 60.67 0.2736 0.57 103% One Example 11 2a 60.69 0.2734 0.57 105% One Example 12 2b 60.62 0.2733 0.57 101% One Comparative Example 3 Comparative compound 1 60.48 0.2733 0.57 100% 5 Comparative Example 4 Comparative compound 2 60.54 0.2735 0.57 99% 2

As shown in Table 3, the colored photosensitive resin composition using the pigment dispersion containing the triazine derivative of the present invention exhibited excellent Y value (transmittance) as compared with the colored photosensitive resin composition using the pigment dispersion containing the compound of the comparative example, Also, it was confirmed that it has excellent relative luminance value.

Claims (11)

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

(In the formula 1,
X ₁ to X ₂ are each 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 a (C6-C12) aryl group or a (C3-C12) heteroaryl group;
Z is Cl, OH,

,

,

or

Lt;
R ₁ to R ₅ 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 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;
c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;
R is 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) alkoxy group, a halo (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxycarbonyl group, C12) _{aryl, -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 to each other -C12) 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 may be different from or the same as each other;
The aryl or heteroaryl group of Ar ₁ may be substituted with at least one substituent selected from the group consisting of halogen, nitro, carboxylic acid, (C 1 -C 5) alkyl, 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,
X ₁ and X ₂ are independently of each other -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-;
Ar ₁ And Z are the same as each other.

(Wherein R ₁ to R ₅ 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) 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 each independently Hydrogen, (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;
c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other.) The method according to claim 1,
In Formula 1,
X ₁ and X ₂ are independently of each other -NH-, -O-, -CONH-, -SO ₂ -, -SO ₂ NH- or -CH ₂ NH-;
Z is Cl or OH;
Ar ₁ Is a triazine derivative selected from the following structures.

(In the above structural formula, R ₁ to R _5, independently of each other, an amino group, a halogen, a nitro group, a carboxyl group, (C1-C5) alkyl, (C1-C5) alkoxy groups, halo (C1-C5) alkyl group, (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;
c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other.) The method according to claim 1,
(1) is a triazine derivative represented by the following general formulas (2) to (3).
(2)

(3)

(In the above formulas 2 and 3,
X ₁ to X ₂ are each 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- ;
Z is Cl, OH,

,

,

or

Lt;
R ₁ to R ₅ 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 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;
c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;
R is 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) alkoxy group, a halo (C 1 -C 5) alkyl group, a (C 1 -C 5) alkoxycarbonyl group, C12) _{aryl, -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 to each other -C12) 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, Rs may be different from or the same as each other. 5. The method of claim 4,
In the general formulas (2) and (3), X ₁ to X ₂ are -NH-;
Z is Cl, OH,

or

Lt;
R ₁ to R ₂ are, each independently, 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 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 N;
c is 0 or an integer of 1 to 3, d is 0 or an integer of 1 to 6, e is 0 or an integer of 1 to 4, and c, d and e are an integer of 2 or more, each of R ₁ , R ₂ and R ₄ may be the same or different from each other;
R is independently selected from the group consisting of a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1- C12) aryl group. 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.