KR102595468B1 - 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 dispersion aid containing the same, and a pigment dispersion containing the same. The triazine derivative of the present invention has excellent dispersibility and improves the dispersibility and storage stability of the pigment dispersion containing the same. Therefore, the colored photosensitive resin composition employing the pigment dispersion of the present invention has excellent optical properties.

Description

Triazine derivatives with high pigment affinity, pigment dispersing aid containing the same and 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. More specifically, it relates to a triazine derivative, a pigment dispersion aid containing the same, a pigment dispersion containing the pigment dispersion aid, and a pigment dispersion. It relates to a colored photosensitive resin composition containing.

Color filters used in liquid crystal display devices are manufactured by forming patterns of three primary colors, that is, red, green, and blue, on a glass substrate.

The process of manufacturing a color pattern includes uniformly applying a photosensitive coloring composition (color resist) containing a colorant corresponding to each color pixel on a substrate, and heating and drying the applied composition to form a film. It consists of selectively exposing the dried film to light using a mask of a desired shape and then developing it, and heating and curing the developed film.

It is common to mainly use pigments as colorants for photosensitive resin compositions used in these processes.

Meanwhile, according to the recent trend of display technology innovation, pigment dispersions with high transmission (brightness) and high contrast characteristics are required to save display power for liquid crystal display devices, and also expand the color gamut. In order to achieve this, the goal is to achieve high color reproduction rate.

To achieve this goal, the concentration of the pigment must be high, but a high concentration of the pigment reduces the storage stability of the pigment dispersion itself and the fairness of the pattern even when turned into a resist, so a high level of pigment dispersion is required. .

In addition to pigments, dispersants, and resins, pigment dispersions use pigment dispersion aids that stabilize the pigment surface. The pigment dispersion aid stabilizes the pigment surface, preventing the storage of the pigment dispersion and the sublimation of the pigment. Additionally, the pigment dispersion aid can be applied during pigment surface treatment to further stabilize the pigment surface, making the pigment very efficient. It can be dispersed.

However, most existing pigment dispersion aids apply substituent changes to the same matrix skeleton as the pigment, so that the molecule as a whole has a different structure from the pigment, and the color spectrum of the pigment and the existing pigment dispersion aid changes, resulting in the color characteristics of the pigment dispersion. This decreases slightly. As a result, the luminance of the image displayed on the display is lowered, which does not meet the current display development goal of low power consumption.

Conventionally, pigment dispersants or dispersion aids using a triazine ring as the parent skeleton are known, but the known structure is limited to the role of a pigment surface treatment agent, and a pigment dispersion aid with improved properties is still required.

Republic of Korea Patent Publication No. 10-2012-0022565 Republic of Korea Patent Publication No. 10-2011-0013320

The present invention provides a triazine compound that can be added to a pigment dispersion and used as a pigment dispersion aid or pigment surface treatment agent to improve storage stability and dispersibility.

The present invention also provides the preparation of a pigment dispersion comprising the triazine compound of the present invention.

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

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

The present invention provides a triazine derivative useful as a dispersion aid and pigment surface treatment agent with high heat resistance and excellent storage stability without affecting the original spectrum of the pigment. The triazine derivative of the present invention is represented by the following formula (1).

[Formula 1]

(In Formula 1 above,

_{X 1 to _ _ _ _ _} and;

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

Z is Cl, OH, , , or and

R ₁ to R ₅ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;

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

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

R is independently of one another halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (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)alkyl, or (C6). -C12) is an aryl group;

a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and 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 group or heteroaryl group of Ar ₁ includes halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, and (C1-C5) alkoxycarbohydrate. It may be substituted with one or more selected from a nyl group, (C6-C12)aryl group, -SO ₂ N(R ₁₁ )(R ₁₂ ) and -CON(R ₁₃ )(R ₁₄ ).)

_{Preferably ,} in Formula ₁ according _to an embodiment of the present invention _, -is;

Ar ₁ and Z may be selected from the following structures in the same manner as each other.

(In the above structural formula, R ₁ to R ₅ are each independently selected from an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1-C5) alkyl group, ( C1-C5) alkoxycarbonyl group, (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 of each other. hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;

D ₁ to D ₄ are each independently CR ₁₅ R ₁₆ or N, and R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (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 when c, d and e are integers of 2 or more, R ₁ , R ₂ and R respectively 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 and 3.

[Formula 2]

[Formula 3]

(In Formulas 2 and 3 above,

_{X 1 to _ _ _ _ _} and;

Z is Cl, OH, , , or and

R ₁ to R ₅ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;

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

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

R is independently of one another halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (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)alkyl, or (C6). -C12) is an aryl group;

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

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

Z is Cl, OH, or and

R ₁ to R ₂ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;

D ₁ is N;

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

R is each independently a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6- C12) It may be an aryl group.

The present invention also provides a pigment dispersion aid containing the triazine derivative of the present invention.

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

The present invention also provides a pigment dispersion liquid containing 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, the pigment dispersant is 10 to 60 parts by weight in solid content based on 100 parts by weight of the pigment, and the pigment dispersion aid is a pigment. It may be included in an amount of 1 to 25 parts by weight per 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 effectively protects the surface of the pigment when applied as a pigment dispersion aid or pigment surface treatment agent, minimizing damage to pigment particles, thereby producing a display device (display) employing a pigment dispersion containing the triazine derivative of the present invention. is capable of producing high-brightness colors.

In addition, the triazine derivative of the present invention has excellent heat resistance, which increases the storage stability of the pigment dispersion containing it, and has an excellent ability to suppress pigment aggregation, thereby significantly increasing the color development luminance of the colored photosensitive resin composition employing the pigment dispersion containing it. improve it.

In addition, the triazine compound of the present invention can be used as a pigment surface treatment agent to turn the prepared pigment into a micropigment, and the produced micropigment is suppressed from re-agglomeration, thereby increasing the dispersibility of the pigment dispersion containing it.

In addition, the pigment dispersion containing the pigment dispersion aid of the present invention also has high storage stability and excellent dispersibility, so the colored photosensitive resin composition using it has high brightness and high color clarity, and has excellent dispersibility even at high concentrations, enabling the implementation of low-power display devices. possible.

The present invention provides a triazine derivative that is used as a pigment dispersion aid or pigment surface treatment agent to improve dispersibility and storage stability and stabilize the pigment surface to improve the brightness and color vividness of displays employing it. Azine derivatives are represented by the following formula (1).

[Formula 1]

(In Formula 1 above,

_{X 1 to _ _ _ _ _} and;

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

Z is Cl, OH, , , or and

R ₁ to R ₅ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;

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

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

R is independently of one another halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (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)alkyl, or (C6). -C12) is an aryl group;

a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and 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 group or heteroaryl group of Ar ₁ includes halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, and (C1-C5) alkoxycarbohydrate. It may be substituted with one or more selected from a nyl group, (C6-C12)aryl group, -SO ₂ N(R ₁₁ )(R ₁₂ ) and -CON(R ₁₃ )(R ₁₄ ).)

The triazine derivative of the present invention has high heat resistance and storage stability when used as a pigment dispersion aid and pigment surface treatment agent, and combines with various functional groups on the surface of the pigment to dramatically improve dispersibility, so displays such as color filters employing it have dramatically improved dispersibility. It has excellent luminance and color clarity.

Specifically, the triazine derivative of the present invention has various functional groups on the surface of the pigment when used as a pigment surface treatment agent by introducing a specific substituent, which is a pigment matrix, a starting material or an intermediate during pigment production, rather than an acidic group or a substituent of the pigment, into the triazine skeleton. When combined or used as a pigment dispersion aid, dispersibility can be improved by improving the bonding strength with various dispersants and dispersing resins.

Unlike compounds with a triazine skeleton used as conventional pigment dispersion aids, the triazine derivative of the present invention introduces an acidic group into the triazine skeleton that can improve the binding force with dispersants and dispersing resins, and is a pigment with high affinity for pigments. By introducing a specific functional group (Z in the formula 1 of the present invention, specifically phthalimide derivatives, quinoline derivatives, etc.) having a similar structure to the matrix or pigment matrix, the pigment dispersion containing the triazine derivative of the present invention has dispersibility and storage. The stability has been dramatically improved, and the colored photosensitive resin composition using this has high brightness, high contrast value, and low power.

Furthermore, the triazine derivative of the present invention introduces a specific functional group that can be combined with pigments, dispersants, and dispersible resins and at the same time increases affinity with pigments, so that when used as a pigment surface treatment agent, the crude pigment can be easily converted into a fine pigment. When used as a pigment dispersion aid, it can protect the pigment surface by combining with various functional groups of the pigment, and can dramatically improve dispersibility by combining with dispersants and dispersing resins.

In terms of improving dispersibility _, preferably in Formula ₁ according to an embodiment of the present invention _{, 2} NH- or -CH ₂ NH-; Ar ₁ and Z may be selected from the following structures in the same manner as each other.

(In the above structural formula, R ₁ to R ₅ are each independently selected from an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1-C5) alkyl group, ( C1-C5) alkoxycarbonyl group, (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 of each other. hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;

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

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

More preferably, in Formula ₁ according _to an embodiment of the present _invention , X _{1 and} is 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 are each independently selected from an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (C6-C12) aryl group, -SO ₂ N(R ₁₁ )(R ₁₂ ) or -CON(R ₁₃ )(R ₁₄ ), and R ₁₁ to R ₁₄ are independent of each other It is hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;

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

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

In terms of dispersibility and storage stability, Formula 1 according to an embodiment of the present invention may be represented by Formulas 2 to 3 below.

[Formula 2]

[Formula 3]

(In Formulas 2 and 3 above,

_{X 1 to _ _ _ _ _} and;

Z is Cl, OH, , , or and

R ₁ to R ₅ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;

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

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

R is independently of one another halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (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)alkyl, or (C6). -C12) is an aryl group;

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

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

Z is Cl, OH, or and

R ₁ to R ₂ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;

D ₁ is N;

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

a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and 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 each independently a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6- C12) It may be an 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 structural formula according to an embodiment of the present invention, Cl(OH) means that Cl is the main product, but OH is included as a by-product. In a specific example, it is very difficult to separate these two compounds, so the by-product is This means that a compound with phosphorous OH is included.

Substituents containing “alkyl,” “alkoxy,” and other “alkyl” moieties described in the present invention include both straight-chain or branched forms.

“Haloalkyl” as used in the present invention refers to an alkyl group in which one or more halogens are substituted, and examples include trifluoromethane and bromomethane.

In addition, “aryl” described in the present invention is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen, and is a single or fused radical containing 6 to 20 ring atoms, preferably 6 or 12, in each ring. It includes a ring system and even includes forms in which multiple aryls are connected by single bonds. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, etc., and examples include phthalimide and unsaturated indene (2H-indene-) described in the present invention. 1,3-dione, 2,3-hydro-1H-indene), isoindoline, etc. are also included in the aryl group.

“Heteroaryl” described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P(=O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. It refers to an aryl group, which is a 5- to 6-membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes forms in which one or more heteroaryls are linked by a single bond.

“Alkenyl” as used herein means a straight-chain or branched-chain hydrocarbon radical containing 2 to 5 carbon atoms and at least one carbon-to-carbon double bond.

The triazine compound described in the present invention can be prepared by any method within the range recognized by a person skilled in the art.

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

In general, the amount of the sulfonic acid compound used per 1 mol of cyanuric chloride may be 0.5 to 1.5 mol, preferably 0.9 to 1.1 mol, and the reaction between cyanuric chloride and the sulfonic acid compound may be performed, for example, by stirring in an appropriate solvent or Without stirring, the reaction was terminated after stirring at -10 to 0°C for 1 to 2 hours. The solvent can be any commonly used solvent, but for example, organic solvents such as water, acetone, dioxane, xylene, dimethylformamide, tetrafluorofuran, or a mixed solvent of two or more types can be used.

Next, at least one compound having one or more amino groups is reacted with the reactant into which the sulfonic acid group has been introduced to introduce a specific functional group that is a pigment matrix, a starting material for producing a pigment, or an intermediate. Specific examples of such compounds include 4-aminophthalimide. The amount of the compound having at least one amino group used per 1 mol of the reaction product between cyanuric chloride and the sulfonic acid compound is appropriately selected depending on the type of compound used, but may be 0.5 to 2.0 mol, preferably 0.9 to 1.5 mol. . In the reaction to introduce such a functional group into the triazine skeleton into which an acidic group has been introduced, organic acids such as acetic acid, benzoic acid, citric acid, fumaric acid, gluconic acid, and oxalic acid, or inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid may be used as solvents. These acids are preferably used in the form of an aqueous solution.

This reaction is terminated in 1 to 10 hours at 30 to 100°C with or without stirring in an appropriate solvent. As the solvent, the same solvent used in the reaction between cyanuric chloride and a sulfonic acid compound can be used. A triazine having an acidic group and two different or the same specific functional groups can be prepared by further reacting a specific functional group having an amino group with the triazine skeleton into which an acidic group and a specific functional group are introduced. Accordingly, a triazine derivative into which a functional group is introduced, which is a pigment matrix, a starting material or an intermediate in the production of a pigment, is produced. The obtained triazine derivative can be easily purified from the reaction mixture by conventional separation and purification means, for example, filtration, washing with water, and drying.

Preferably, in order to improve dispersibility, the triazine derivative of the present invention is introduced into a pigment base having high affinity for an acidic group and a pigment, or a starting material or intermediate during the production of the pigment. For example, the triazine derivative of the present invention is an acidic group and a pigment matrix, and when introducing phthalimide and quinoline such as compounds 1a, 1, 2a and 2b described in the present invention, which are functional groups as starting materials or intermediates during the production of pigments, is preferably used as a pigment dispersion aid and surface treatment agent for phthalimide-based pigments and quinoline-based pigments containing phthalimide and quinoline, for example, Pigment Yellow 138, When introducing the derivative represented by as a functional group, it is more preferable to use it as a pigment dispersion aid and surface treatment agent for Pigment Red 254, 255, 264, 270, 272 and Pigment Orange 71, 73, and 81.

The present invention also provides a pigment dispersion aid containing the triazine derivative of the present invention.

The pigment dispersion aid of the present invention has high dispersibility and storage stability by using the triazine derivative of the present invention, so the pigment dispersion containing it has high dispersion, and is manufactured using a colored photosensitive resin composition containing such a pigment dispersion. Displays such as color filters have high brightness and excellent contrast values.

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

The pigment surface treatment agent of the present invention contains the triazine derivative of the present invention, which is capable of combining with various functional groups of the pigment and has a remarkable effect of suppressing damage to the surface of the pigment and suppressing aggregation between the prepared pigments, thereby easily converting the prepared pigment into a pigment. Fine pigments can be manufactured.

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

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

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

The pigment contained in the pigment dispersion according to an embodiment of the present invention is not limited as long as it is an organic pigment, but may be an azo pigment or a condensation pigment, and may be used alone or in combination of two or more types.

Specifically, the red pigment is C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 49, 57, 60, 63, 64, 68, 69, 81, 83, 88, 101, 104, 108, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 2 09, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 2 55, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 272, 272, 273, 274, 275, 276, etc. Among these, preferred C.I. Pigment Red , 122, 166, 168, 177, 179 202, 206, 207, 209, 224, 242, 254, 264, 269, etc., more preferably C.I. Pigment Red 166, 177, 179, 209, 224, 254, 264, 269, etc. are included.

The green pigment is 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, 59, etc. Preferably C.I. Pigment Green 7, 36, 58, 59, etc. are included.

The yellow pigment is C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 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, 1 53, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 1 88, Examples include 193, 194, 199, 198, 213, and 214. Among these, preferably C.I. Pigment Yellow 129, 138, 185, etc. may be mentioned.

The orange pigment is 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, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, etc., preferably C.I. Examples include Pigment Orange 38, 71, and 73.

The pigment according to an 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.

In addition, the pigment contained in the pigment dispersion of the present invention can be obtained by reacting a compound that is a raw material of an organic pigment in the presence of a pigment surface treatment agent containing the triazine derivative of the present invention or by turning a crude pigment into a pigment.

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

In the present invention, the crude pigment is a compound obtained by reacting the raw material compounds that form the basis of the condensed polycyclic pigment and has a large particle diameter (for example, about 10 to several hundred ㎛), which itself has the dispersibility and vivid color as a pigment. This means that color development is not achieved. Preparation pigments of these condensed polycyclic pigments can be prepared by known methods.

In the present invention, the above-mentioned crude pigment can be pigmented in the presence of the triazine derivative. Pigmentation in the present invention means a process of adjusting the particle diameter of the prepared pigment to an appropriate particle diameter range as a pigment. Additionally, the appropriate particle range varies depending on the use, etc., but may be 0.05 to 0.3㎛.

Additionally, as a method of pigmentation, a known method such as salt milling can be used. There is no particular limitation on the amount of the triazine derivative added during pigmentation, but the triazine derivative may be added in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the crude pigment. If the amount of the triazine derivative added is less than 0.1 parts by weight, the effect of inhibiting crystal growth is small, and if it is more than 20 parts by weight, it may affect performance such as transparency and contrast of the final product.

After converting the crude pigment into a pigment, washing it with water and drying it according to a conventional method, and pulverizing it with a disperser such as a roll mill or bead mill, a fine pigment composition containing highly refined condensed polycyclic pigments with a very small primary particle diameter can be obtained.

In the micropigment composition containing the triazine derivative of the present invention and the desired organic pigment obtained as mentioned above, the desired organic pigment is highly refined, for example, the primary particle of the organic pigment has a major axis of 50 to 150 nm, It can be obtained with a minor diameter of 30 to 100 nm.

In addition, the micropigment composition prepared as described above has very small and highly refined primary particles of organic pigments, and can significantly suppress agglomeration. Even when dispersed in a pigment dispersion, aggregation is effectively prevented due to a synergistic effect with dispersants. Therefore, it can be easily applied to colored photosensitive resin compositions for color filters, etc., which have high brightness and excellent contrast value.

The pigment dispersant according to an embodiment of the present invention is commonly used in the production of colored photosensitive resin compositions for color filters, and for example, it is suitable to include an amine group or an ammonium salt group as a pigment affinity group, and a preferred example thereof is an acrylic-based dispersant. Examples include polymers, polyurethanes, polyethylene imines, and mixtures thereof. Commercially available dispersants include BYK-Chemie's Disperbyk-160, Disperbyk-161, Disperbyk-165, Disperbyk-168, Disperbyk-170, Disperbyk-171, and Disperbyk- 2000, Dispervik-2001; Disperbig-LN21116; and dispervic-LPN6919, LPN-22102, LPN-22251, LPN-22238, LPN-22841, LPN-22421, LPN-22470, LPN-22558, LPN-22822, LPN-22964, LPN-22481, LPN-22484, 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, Solsperse-12000, Solsperse-22000, Solsperse-24000, and Solsperse-32500 from AVECIA; and PB-821, PB-822, PB-824, and PB-827 from AJINOMOTO. These dispersants can be used individually or in combination of two or more types.

The pigment dispersant according to an embodiment of the present invention is a pigment based on the solid content of the pigment dispersant in terms of storage stability and problems such as the problem of residue remaining after development due to slow development speed with alkaline developer when manufacturing colored photosensitive resin containing pigment dispersion. It can be used in an amount of 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.

The pigment dispersion according to an embodiment of the present invention may further include an alkali-soluble resin as a dispersing resin, and is commonly used in colored photosensitive resin compositions for color filters, and is a linear polymer that is soluble in organic solvents. Resin is preferred.

Specific examples of monomers that can be used in the acrylic resin include compounds having one or more carboxyl groups in the molecule (eg, acrylic acid, methacrylic acid, maleic acid, fumaric acid); aromatic vinyl compounds (e.g., styrene, α-methylstyrene, vinyltoluene, vinylbenzylmethyl ether, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, etc.); 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); Compounds having hydrophilic properties (e.g., (meth)acrylamide, secondary or tertiary akylacrylamide, 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 phosphate ester moiety, a quaternary ammonium salt moiety, an ethylene oxy chain, a propylene oxy chain, and a sulfonic acid group.

To increase crosslinking efficiency, the resin may have a polymerizable group on the side chain.

The acrylic resin preferably has a weight average molecular weight (measured by GPC method, converted to 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, and more preferably 20 to 50 parts by weight, based on 100 parts by weight of the pigment of the present invention.

As the solvent used in the pigment dispersion according to an embodiment of the present invention, various commonly known solvents can be used without particular limitation. Specific examples 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, diethylene glycol monoethyl ether, and these. acetic acid esters, ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone, and cyclohexanone, gamma-butyrolactone, ethyl lactate, butyl lactate, and ethyl pyruvate. These solvents can be used individually 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 organic acid as an additive to improve the dispersion stability, heat stability, and alkali developability of the pigment.

As the surfactant used in the pigment dispersion according to an embodiment of the present invention, various commonly known surfactants can be used without particular limitation, and commercially available surfactants include Megafac R08 and Megafac F477 (Dainipon (manufactured by Ink & Chemicals), etc.

The pigment dispersion of the present invention has high storage stability and dispersibility by containing the triazine derivative of the present invention, thereby significantly improving the brightness and contrast ratio characteristics of displays such as color filters using colored photosensitive resin compositions employing the triazine derivative of the present invention.

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 typically be a colorant, and the colorant may be a pigment, dye, or a mixture thereof.

The pigments described above can be used, and the dyes can be any dyes commonly used as colorants. Specific examples 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; There are acid oranges 6, 7, 8, 10, 12, 26, 51, 52, 62, 63, 64, 74, 107, 169, etc.

The colored photosensitive resin composition according to an embodiment of the present invention may further include a photoinitiator and a crosslinking agent, and as the photoinitiator used in the present invention, various commonly known photoinitiator compounds may be used without particular limitation. Specific examples thereof include iodine salt compounds, sulfonium salt compounds, organic halogen compounds, oxime compounds, and mixtures thereof. Commercially available photoinitiators include Irgacure-907, Irgacure-369, Irgacure OXE 01, and Irgacure OXE 02 from Ciba Geigy. The photoinitiator may be preferably used in an amount of 0.1 to 5% by weight based on the total weight of the colored photosensitive resin composition. Each photoinitiator can be used individually or in combination of two or more types. The cross-linking agent used in the present invention can be any of various commonly known cross-linking agent compounds without particular restrictions. Specific examples include ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate having 2 to 14 ethylene groups, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, Pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 2-trisacryloyloxymethylethylphthalic acid, propylene glycol di(meth)acrylate, polypropylene glycol di having 2 to 14 propylene groups. (meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. These crosslinking agents can be used individually or in combination of two or more. The crosslinking agent may be preferably used in an amount of 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 coloring power and can be very useful in the production of a low-power, high-color reproduction color filter.

Hereinafter, the present invention will be described in detail by examples. However, the following examples are merely illustrative of the present invention and the content of the present invention is not limited to the following examples.

[Example 1] Preparation of triazine derivative 1a

Cyanuric chloride (9.3 g) was dissolved in 500 mL of acetone, and sulphanilic acid (8.6 g) in an amount that reacts with one chlorine atom of cyanuric chloride was added and reacted at 0°C for 1 hour. 4-amino phthalimide (8.1 g) was added thereto and reacted at 40°C for 1 hour. Then, 4-amino phthalimide (8.1 g) was additionally added and reacted at 90°C for 5 hours. The obtained reaction product was leached and the resulting residue was washed with water, left in a thermostat at 100°C overnight and dried to obtain the target product, triazine compound 1a (20.2 g). (LC/MS, m/z=572)

[Example 2] Preparation of triazine derivative 1b

Compound 1b, (20.07) g was obtained in the same manner as in Example 1, except that the reaction was carried out without further adding 4-aminophthalimide. (LC/MS, m/z=446)

[Example 3] Preparation of triazine derivative 2a

Compound 2a, (19.1) g was obtained in the same manner as in Example 1, except that 8-amino quinoline (7.2 g) was added instead of 4-aminophthalimide in Example 1. . (LC/MS, m/z=536)

[Example 4] Preparation 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 further adding 8-aminoquinoline. (LC/MS, m/z=428)

[Examples 5 to 8] Preparation of pigment dispersion

The ingredients and usage amounts shown in Table 1 below were put into a mixer with an net capacity of 1000 mL, 360 g of zirconia beads with a diameter of 1.0 mm were added, and stirred with a disper at 200 rpm for 60 minutes to prepare a preliminary dispersion. did.

ingredient Usage (g) C.I. Pigment Yellow 138 40.00g Triazine compound 1a of the present invention 1.20g Pigment dispersant (Product name: BYK LPN-22102, solids concentration 38.7%) 31.01g Dispersible resin (Product name: Showa 19X, solids concentration 27.9%) 71.68g PGMEA (Propylene Glycol Monomethyl Ether Acetate) 96.11g

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

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

[Comparative Examples 1 to 2]

Pigment was prepared in the same manner as in Example 4, except that in Example 5, the pigment dispersion was prepared using Comparative Example Compound 1 below or Comparative Compound 2 below instead of the triazine compound prepared in Example 1 of the present invention. A dispersion was prepared.

Comparative compound 1 was prepared as follows.

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

Elemental analysis (C27H7Cl8NO7S) calculated: C 41.95; H 0.91; Cl 36.69; N 1.81; O 14.49; S 4.15; Measurements: C 41.90; H 0.96; Cl 36.63; N 1.74; O 14.40; S 4.06

Comparative Compound 2 below was prepared in the same manner as disclosed in Korea Patent Publication No. 2011-0013320.

Cyanuric chloride (9.3) g was dissolved in 500 mL of acetone, and sulfanilic acid (8.6 g) in an amount that reacts with one chlorine atom of cyanuric chloride was added and reacted at 0°C for 1 hour. Here, 4,4'-methylenebis(2,6-dimethylaniline) (15.8g) was added and reacted at 40°C for 1 hour. The obtained reactant was leached. The resulting residue was washed with water, left in a thermostat at 100°C overnight, and dried to obtain the target Comparative 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 ingredients and contents shown in Table 2 below were placed in a mixer with an net capacity of 1000 mL, 360 g of zirconia beads with a diameter of 1.0 mm were added, and stirred with a disper at 200 rpm for 60 minutes to prepare a preliminary dispersion. did.

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

ingredient Usage (g) C.I. Pigment Green 58 40.00g Resin-type dispersant (Product name: BYK LPN-22251, solids concentration 41.2%) 29.13g Resin-type dispersant (Product name: Showa 19X, solids concentration 27.9%) 71.68g PGMEA (Propylene Glycol Monomethyl Ether Acetate) 97.99g

Each colored photosensitive resin composition was prepared by mixing the yellow pigment dispersion obtained in Examples 5 to 8 with the green pigment dispersion obtained above in a ratio of 4:6 (weight ratio), and the obtained colored photosensitive resin composition was coated using a spin coater. After forming the film, it was dried on a hot-plate at 100°C for 10 minutes to obtain a coating film. The obtained coating film was exposed to light of 100 mJ/cm ² using an ultra-high pressure mercury lamp, developed with an alkaline developer, and then washed with ultrapure water. The developed coating film was heat-cured (post-bake) in an oven at 230°C for 20 minutes to form a pattern for a color filter. The chromaticity (x, y, Y) of the heat-cured coating film was measured using a colorimeter MCPD-3000 (manufactured by Otsuka Corporation), and the results are shown in Table 3 below.

Colored photosensitive resin composition Triazine derivatives used in pigment dispersions Y x y CR(%) Sublimable substances
(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 exhibits an excellent Y value (transmittance) compared to the colored photosensitive resin composition using the pigment dispersion containing the compound of the comparative example, It was also confirmed that it had excellent relative luminance value.

Claims (11)

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

(In Formula 1 above,
i) X ₁ and X ₂ are -NH-,
Ar ₁ is selected from the structures below,

Z is , , or This is,
ii) X ₁ is -NH-,
Ar ₁ is selected from the structures below,

-X ₂ Z is Cl or OH;
R ₁ to R ₅ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;
D ₁ to D ₄ are each independently CR ₁₅ R ₁₆ or NH, and R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (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 when c, d and e are integers of 2 or more, R ₁ , R ₂ and R respectively ₄ may be the same or different from each other;
R is independently of one another halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (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)alkyl, or (C6). -C12) is an aryl group;
a is 0 or an integer from 1 to 5, b is an integer from 1 to 5, and 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 group or heteroaryl group of Ar ₁ includes halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, and (C1-C5) alkoxycarbohydrate. It may be substituted with any one or more selected from a nyl group, (C6-C12)aryl group, -SO ₂ N(R ₁₁ )(R ₁₂ ), and -CON(R ₁₃ )(R ₁₄ ).) According to clause 1,
In Formula 1,
X ₁ and X ₂ are -NH-;
A triazine derivative in which Ar ₁ and Z are equally selected from the structures below.

(In the above structural formula, R ₁ to R ₅ are each independently selected from an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1-C5) alkyl group, ( C1-C5) alkoxycarbonyl group, (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 of each other. hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;
D ₁ to D ₄ are each independently CR ₁₅ R ₁₆ or NH, and R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (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 when c, d and e are integers of 2 or more, R ₁ , R ₂ and R respectively ₄ may be the same or different from each other.) According to clause 1,
In Formula 1,
X ₁ is -NH-;
-X ₂ Z is Cl or OH;
Ar ₁ is a triazine derivative selected from the structures below.

(In the above structural formula, R ₁ to R ₅ are each independently selected from an amino group, a halogen group, a nitro group, a carboxylic acid group, a (C1-C5) alkyl group, a (C1-C5) alkoxy group, a halo (C1-C5) alkyl group, (C1-C5)alkoxycarbonyl group, (C6-C12)aryl group, -SO ₂ N(R ₁₁ )(R ₁₂ ) or -CON(R ₁₃ )(R ₁₄ ), and R ₁₁ to R ₁₄ are independent of each other It is hydrogen, (C1-C5)alkyl or (C6-C12)aryl group;
D ₁ to D ₄ are each independently CR ₁₅ R ₁₆ or NH, and R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (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 when c, d and e are integers of 2 or more, R ₁ , R ₂ and R respectively ₄ may be the same or different from each other.) According to clause 1,
The above formula (1) is a triazine derivative represented by the following formulas (2) and (3).
[Formula 2]

[Formula 3]

(In Formulas 2 and 3 above,
i) X ₁ to X ₂ are -NH-,
Z is , , or This is,
ii) X ₁ is -NH- and -X ₂ Z is Cl or OH;
R ₁ to R ₅ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;
D ₁ to D ₄ are each independently CR ₁₅ R ₁₆ or NH, and R ₁₅ and R ₁₆ are independently hydrogen, (C1-C5) alkyl group, (C1-C5) alkoxy group, or halo (C1-C5) alkyl group. , (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 when c, d and e are integers of 2 or more, R ₁ , R ₂ and R respectively ₄ may be the same or different from each other;
R is independently of one another halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, (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)alkyl, or (C6). -C12) is an aryl group;
a is 0 or an integer from 1 to 5, b is an integer from 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.) According to clause 4,
In Formulas 2 and 3, i) X ₁ and X ₂ are -NH-,
Z is or or ii) X ₁ is -NH- and -X ₂ Z is Cl or OH;
R ₁ to R ₂ are independently of each other, amino group, halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) An alkoxycarbonyl group, (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) alkyl or (C6-C12) aryl group;
D ₁ is NH;
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 when c, d and e are integers of 2 or more, R ₁ , R ₂ and R respectively ₄ may be the same or different from each other;
R is each independently a halogen group, nitro group, carboxylic acid group, (C1-C5) alkyl group, (C1-C5) alkoxy group, halo (C1-C5) alkyl group, (C1-C5) alkoxycarbonyl group, or (C6- C12) Aryl group triazine derivative. A pigment dispersion aid comprising the triazine derivative of any one of claims 1 to 5. A pigment surface treatment agent comprising the triazine derivative of any one of claims 1 to 5. A pigment dispersion containing the pigment dispersion aid, pigment, pigment dispersant and solvent of claim 6. According to clause 8,
The pigment is a pigment dispersion having a volume average particle diameter of 10 to 150 nm. According to clause 8,
The pigment dispersant is 10 to 60 parts by weight in solid content based on 100 parts by weight of the pigment, and the pigment dispersion aid is 1 to 25 parts by weight based on 100 parts by weight of the pigment. A colored photosensitive resin composition comprising the pigment dispersion according to claim 8.