KR20160091878A - Novel polymer, colorant including the same, positive photosensitive resin composition including the same and color filter - Google Patents

Abstract

Provided is a monomer produced by a co-polymerization reaction between a compound represented by chemical formula 1 and at least one monomer selected from the group composed of an ethylenic unsaturated monomer, an isocyanate monomer, an alcohol monomer, and a combination thereof. Also, provided are a colorant including the same, a photosensitive resin composition including the colorant, and a color filter. In the chemical formula 1, each substituent is the same as defined in the present specification.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel polymer, a colorant containing the same, a photosensitive resin composition containing the same, and a color filter comprising the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a novel polymer, a colorant containing the same, a photosensitive resin composition containing the same, and a color filter.

The development of the optical display device industry is proceeding in order to realize a high contrast ratio and a high brightness so as to provide a clearer and higher quality screen with low power.

Conventional color filters use a pigment dispersion as a colorant, and the non-uniformity between such a pigment and the photoresist composition causes a reduction in the contrast ratio of the color filter. Further, since conventional pigments have a limited chromophore structure, it is difficult to realize various colors with such a limited pigment material, and it is difficult to expect a large improvement in transmittance in a specific color.

Accordingly, attempts have been made to introduce dye-type colorants to overcome these limitations, and it is necessary to develop dye-type materials having good color characteristics, good solubility, and satisfactory reliability.

One embodiment is to provide a novel polymer.

Another embodiment is to provide a colorant comprising the polymer.

Another embodiment is to provide a photosensitive resin composition comprising the colorant.

Another embodiment is to provide a color filter made from the photosensitive resin composition.

One embodiment provides a polymer wherein a compound represented by the following formula (1) is copolymerized with an 'ethylenically unsaturated monomer, an isocyanate monomer, an alcohol monomer, or a combination thereof.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (2), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (2)

(2)

In Formula 2,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,

Y is a single bond, -O-, -C (═O) -, -C (═O) R'-, -OR "-, -R" O- or -OC -, wherein R 'to R' "each independently represent a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,

Z is a substituted or unsubstituted acrylate group, a substituted or unsubstituted amine group, an isocyanate group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group or -OC (= O) R '' ' '' 'Is a substituted or unsubstituted C1 to C20 alkyl group,

n is an integer of 1 or 2;

R ⁵ and R ⁶ may be represented by the general formula (2).

The polymer is an acrylic polymer, and the acrylic polymer may be formed by a copolymerization reaction of a compound represented by the following formula (1) and an ethylenic unsaturated monomer.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (3), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (3)

(3)

In Formula 3,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

R ⁹ is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n1 is an integer of 1 or 2;

Wherein said ethylenically unsaturated monomer is at least one selected from the group consisting of an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, It can be any one selected.

The polymer is an urea polymer, and the urea polymer may be formed by a copolymerization reaction of a compound represented by the following formula (1) and an isocyanate monomer.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula 4, provided that at least one of R ⁵ and R ⁶ is represented by the following formula 4,

[Chemical Formula 4]

In Formula 4,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

R ¹⁰ and R ¹¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n2 is an integer of 1 or 2;

The polymer is a urethane polymer, and the urethane polymer may be formed by a copolymerization reaction of a compound represented by the following formula (1) and an alcohol monomer.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (5), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (5)

[Chemical Formula 5]

In Formula 5,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

n3 is an integer of 1 or 2;

The polymer is a urethane polymer, and the urethane polymer may be formed by a copolymerization reaction between a compound represented by the following formula (1) and an isocyanate monomer.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (6), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (6)

[Chemical Formula 6]

In Formula 6,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

n4 is an integer of 1 or 2;

The formula (2) may be represented by any one of the following formulas (7) to (10).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

 In the above Chemical Formulas 7 to 10,

L is a single bond, a divalent or trivalent aliphatic organic group, or a divalent or trivalent alicyclic organic group,

R ^a to R ^g are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n5 is an integer of 1 or 2,

m1 to m4 and m6 are each independently an integer of 0 to 15,

m5 is an integer of 1 to 5;

Another embodiment provides a colorant comprising the polymer.

Another embodiment provides a photosensitive resin composition comprising the colorant.

The photosensitive resin composition may further comprise a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

Another embodiment provides a color filter made from the photosensitive resin composition.

As the polymer has excellent heat resistance and solubility, high color transmittance and high contrast ratio, it is possible to produce a color filter excellent in luminance, solvent resistance and heat resistance from a photosensitive resin composition containing a colorant containing the polymer as a component have.

1 is a graph showing the permeability of a methanol solution containing 1% by weight of a compound represented by the general formula (3-1).
2 is a graph showing the permeability of a methanol solution containing 1% by weight of a compound represented by Formula 6-3.
3 is a graph showing the permeability of a methanol solution containing 1% by weight of a compound represented by the formula (7-1).
4 is a graph showing the permeability of a methanol solution containing 1 wt% of a compound represented by the formula 7-2.
5 is a graph showing the permeability of a methanol solution containing 1 wt% of a compound represented by the formula 8-1.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Br, Cl or I), a hydroxyl group, a nitro group, a cyano group, an amine group ^{_{(NH 2, NH (R 200}} ) , or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, being each independently selected from C1 to C10 alkyl groups), amidino group , Hydrazine group, hydrazone group, carboxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted alicyclic alkyl group, substituted or unsubstituted aryl group , And a substituted or unsubstituted heterocyclic group.

Unless otherwise specified in the specification, "alkyl group" means C1 to C30 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C30 cycloalkyl group, specifically C3 Refers to a C1 to C30 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C30 aryl group, specifically, a C6 to C30 aryl group, C18 aryl group, "alkenyl group" means C2 to C30 alkenyl group, specifically C2 to C18 alkenyl group, "alkylene group" means C1 to C30 alkylene group, specifically C1 Means a C6 to C30 arylene group, and specifically refers to a C6 to C16 arylene group.

Unless otherwise specified in the present specification, the term "aliphatic organic group" means a C1 to C30 alkyl group, a C2 to C30 alkenyl group, a C2 to C30 alkynyl group, a C1 to C30 alkylene group, a C2 to C30 alkenylene group, Means a C1 to C15 alkyl group, a C2 to C15 alkenyl group, a C2 to C15 alkynyl group, a C1 to C15 alkylene group, a C2 to C15 alkenylene group, or a C2 to C15 alkynylene group, Means a C3 to C30 cycloalkyl group, a C3 to C30 cycloalkenyl group, a C3 to C30 cycloalkynyl group, a C3 to C30 cycloalkylene group, a C3 to C30 cycloalkenylene group, or a C3 to C30 cycloalkynylene group. C3 to C15 cycloalkenyl groups, C3 to C15 cycloalkynyl groups, C3 to C15 cycloalkylene groups, C3 to C15 cycloalkenylene groups, Means a C6 to C30 aryl group or a C6 to C30 arylene group, specifically, a C6 to C16 aryl group or a C6 to C16 arylene group, and the term " aromatic hydrocarbon group " "Heterocyclic group" means a C2 to C30 cycloalkyl group containing 1 to 3 hetero atoms selected from the group consisting of O, S, N, P, Si and combinations thereof in one ring, C2 to C30 cycloalkyl Means a C2 to C30 cycloalkenyl group, a C2 to C30 cycloalkenylene group, a C2 to C30 cycloalkynyl group, a C2 to C30 cycloalkynylene group, a C2 to C30 heteroaryl group, or a C2 to C30 heteroarylene group, Specifically, C2 to C15 cycloalkyl groups containing 1 to 3 hetero atoms selected from the group consisting of O, S, N, P, Si and combinations thereof in one ring, C2 to C15 A C2 to C15 cycloalkenyl group, a C2 to C15 cycloalkynylene group, a C2 to C15 cycloalkynylene group, a C2 to C15 heteroaryl group, or a C2 to C15 heteroarylene group, it means.

The "cycloalkenylene group" described in this specification includes "bicycloalkenylene group".

As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.

In the present specification, "*" means the same or different atom or part connected to a chemical formula.

The polymer according to an embodiment is formed by a copolymerization reaction of a compound represented by the following formula (1) and a monomer selected from the group consisting of ethylenically unsaturated monomers, isocyanate monomers, alcohol monomers, and combinations thereof.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (2), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (2)

(2)

In Formula 2,

L is a single bond, a divalent or trivalent aliphatic organic group, or a divalent or trivalent alicyclic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,

Y is a single bond, -O-, -C (═O) -, -C (═O) R'-, -OR "-, -R" O- or -OC -, wherein R 'to R' "each independently represent a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,

Z is a substituted or unsubstituted acrylate group, a substituted or unsubstituted amine group, an isocyanate group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group or -OC (= O) R '' ' '' 'Is a substituted or unsubstituted C1 to C20 alkyl group,

n is an integer of 1 or 2;

또는

일 수 있다.For example, L is a single bond,

or

Lt; / RTI >

R ⁵ and R ⁶ may be represented by the formula (2). In this case, R ⁵ and R ⁶ either both, only one compound, and R ⁵ and R ⁶ represented by the formula (2) becomes of the good compatibility of the organic material than a hydrogen atom in the compound, it is excellent in solubility in an organic solvent.

The formula (2) may be represented by any one of the following formulas (3) to (6).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Chemical Formulas 3 to 6,

L is a single bond, a divalent or trivalent aliphatic organic group, or a divalent or trivalent alicyclic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,

Y is a single bond, -OR "- or -OC (═O) NHR '" -, wherein R "and R'" are each independently a substituted or unsubstituted C1 to C20 alkylene group, An unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,

R ⁹ to R ¹¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n1 to n4 each independently represent an integer of 1 or 2;

The compound containing a functional group represented by any of the above formulas (3) to (6) has high transmittance and is excellent in coloring power and can be usefully used as a colorant.

The compound containing a functional group represented by the formula (3) may be any of compounds represented by the following formulas (3-1) to (3-11), but is not limited thereto.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

[Chemical Formula 3-7]

[Chemical Formula 3-8]

[Chemical Formula 3-9]

[Chemical Formula 3-10]

[Formula 3-11]

The compound containing a functional group represented by the formula (4) may be any one of compounds represented by the following formulas (4-1) to (4-3), but is not limited thereto.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

The compound containing a functional group represented by the formula (5) may be any one of compounds represented by the following formulas (5-1) to (5-3), but is not limited thereto.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

The compound containing a functional group represented by the formula (6) may be any of compounds represented by the following formulas (6-1) to (6-6), but is not limited thereto.

[Formula 6-1]

[Formula 6-2]

[Formula 6-3]

[Formula 6-4]

[Formula 6-5]

[Formula 6-6]

The formula (2) may be represented by any one of the following formulas (7) to (10).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above Chemical Formulas 7 to 10,

L is a single bond, a divalent or trivalent aliphatic organic group, or a divalent or trivalent alicyclic organic group,

R ^a to R ^g are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n5 is an integer of 1 or 2,

m1 to m4 and m6 are each independently an integer of 0 to 15,

m5 is an integer of 1 to 5;

In the above formula (1), when at least one of R ⁵ and R ⁶ is represented by any of the above formulas (7) to (10), the solubility and spectroscopic characteristics may be improved.

The functional group represented by the formula (8) may be represented by any one of the following formulas (A) to (L), but is not limited thereto.

[Chemical Formula A] [Chemical Formula C] [Chemical Formula D]

[Formula F] [Formula G]

[Formula H] < EMI ID =

[Chemical Formula L] [Chemical Formula L]

The functional group represented by the formula (9) may be represented by the following formula (M) or (N), but is not limited thereto.

[Chemical Formula M] [Chemical Formula N]

The compound containing a functional group represented by the formula (7) may be, for example, a compound represented by the following formula (7-1) or (7-2), but is not limited thereto.

[Formula 7-1]

[Formula 7-2]

The compound containing a functional group represented by the formula (8) may be, for example, a compound represented by the following formula (8-1), but is not limited thereto.

[Formula 8-1]

The monomers may be ethylenically unsaturated monomers, isocyanate monomers, alcohol monomers, or combinations thereof.

For example, the ethylenically unsaturated monomer may be an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, have.

For example, the ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide, or combinations thereof.

For example, the isocyanate monomer means a monomer containing an isocyanate group, and commonly known aliphatic or aromatic diisocyanate compounds are all included. Specific examples include 2,2'-diphenylmethane diisocyanate (MDI), 2,4'-diphenylmethane diisocyanate (MDI), 4,4'-diphenylmethane diisocyanate (MDI), polymeric MDI, 1 , 5-naphthylene diisocyanate (NDI), 2,4-2,6-tolylene diisocyanate (TDI), 2,6-tolylene diisocyanate (TDI), 3,3'-dimethyl biphenyl diisocyanate, 1,2-diphenyl ethane diisocyanate, phenyl diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, 2-methylpentamethylene 1 , 5-diisocyanate, 2-ethylbutylene 1,4-diisocyanate, pentamethylene 1,5-diisocyanate, butylene 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl -5-isocyanatomethylcyclohexane ( Bis (isocyanatomethyl) cyclohexane (HXDI), 1,4-cyclohexane (isocyanatomethyl) cyclohexane (HXDI) Diisocyanate, 1-methyl-2,4-cyclohexane diisocyanate, 1-methyl-2,6-cyclohexane diisocyanate, 4,4'-dicyclohexylmethane diisocyanate (H12MDI) (H12MDI), 2,2'-dicyclohexylmethane diisocyanate (H12MDI), and the like.

For example, the above-mentioned alcohol monomer means a monomer containing an alcohol group, specifically, polyesterol, polyetheramine and / or polycarbonate diol compound, and more specifically polyalkylene glycol, more specifically Polytetrahydrofuran (PTHF), polybutylene glycol, polypropylene glycol, polyethylene glycol, and copolymers obtained by the addition reaction of ethylene oxide, butylene oxide and propylene oxide.

The polymer may be an acrylic polymer, a urea polymer or a urethane polymer.

The acrylic polymer may be formed by a copolymerization reaction of the compound represented by the formula (1) containing the functional group represented by the formula (3) and the ethylenically unsaturated monomer.

For example, the compound represented by the formula (1) containing the functional group represented by the formula (3) is as follows.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (3), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (3)

(3)

In Formula 3,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

R ⁹ is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n1 is an integer of 1 or 2;

The urea polymer may be formed by a copolymerization reaction of the compound represented by the formula (1) containing a functional group represented by the formula (4) and the isocyanate monomer.

For example, the compound represented by the formula (1) containing the functional group represented by the formula (4) is as follows.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula 4, provided that at least one of R ⁵ and R ⁶ is represented by the following formula 4,

[Chemical Formula 4]

In Formula 4,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

R ¹⁰ and R ¹¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

n2 is an integer of 1 or 2;

The urethane polymer may be formed by the copolymerization reaction of the compound represented by the general formula (1) containing the functional group represented by the general formula (5) and the alcohol monomer.

For example, the compound represented by the formula (1) containing the functional group represented by the formula (5) is as follows.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (5), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (5)

[Chemical Formula 5]

In Formula 5,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

n3 is an integer of 1 or 2;

The urethane polymer may be formed by a copolymerization reaction of the compound represented by the general formula (1) containing a functional group represented by the general formula (6) and the isocyanate monomer.

For example, the compound represented by the formula (1) containing the functional group represented by the formula (6) is as follows.

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,

R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (6), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (6)

[Chemical Formula 6]

In Formula 6,

L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,

X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,

Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,

n4 is an integer of 1 or 2;

The compound or polymer represented by Formula 1 may be used as a dye.

Another embodiment provides a colorant comprising the compound represented by Formula 1 or the polymer.

Another embodiment provides a photosensitive resin composition comprising the colorant.

The photosensitive resin composition may further comprise a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

Hereinafter, the components will be described in detail.

coloring agent

The colorant may further include an organic solvent soluble dye, in addition to the compound or polymer represented by the formula (1).

Examples of the organic solvent soluble dyes include triarylmethane compounds, anthraquinone compounds, benzylidene compounds, cyanine compounds, phthalocyanine compounds, azapphyrin compounds, and indigo compounds.

The colorant may further include a pigment, in addition to the compound or polymer represented by the formula (1).

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

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

Examples of the purple pigments include CI violet pigment 1, CI violet pigment 19, CI violet pigment 23, CI violet pigment 27, CI violet pigment 29, CI violet pigment 30, CI violet pigment 32, CI violet pigment 37, CI violet pigment 40, CI violet pigment 42, CI violet pigment 50, or a combination thereof.

Examples of the red pigment include pigments such as perylene pigments, anthraquinone pigments, dianthraquinone pigments, azo pigments, diazo pigments, quinacridone pigments, anthracene pigments, and the like. . Specific examples of the red pigments include perylene pigments, quinacridone pigments, naphthol AS, siccone pigments, anthraquinone (sudan I, II, III, R), giant anthraquinone , Vis azo, benzopyran and the like.

Examples of the green pigment include halogenated phthalocyanine pigments such as polychlorotrifthalocyanine and polychlorobromophthalocyanine.

Examples of the yellow pigments include tetrachloroisoindolinone pigments, hansa pigments, benzidine yellow pigments, azo pigments, and the like. Specific examples thereof include hansa yellow (10G, 5G, 3G, G, GR, A, RN, R), benzidine (G, GR), chrome yellow, permanent yellow (FGL, H10G, HR), and anthracene.

Binder resin

The binder resin may be an acrylic binder resin.

The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and is a resin containing at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5% by weight to 50% by weight, for example, 10% by weight to 40% by weight based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.

Specific examples of the acrylic binder resin include (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate / 2- Acrylate copolymer, a (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and the like, but not limited thereto, and they may be used alone or in combination have.

The weight average molecular weight of the acrylic binder resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 2,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the acrylic binder resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties and a suitable viscosity.

The acid value of the acrylic binder resin may be from 15 mgKOH / g to 60 mgKOH / g, such as from 20 mgKOH / g to 50 mgKOH / g. When the acid value of the acrylic binder resin is within the above range, the resolution of the pixel pattern is excellent.

The acrylic binder resin may be contained in an amount of 1% by weight to 30% by weight, for example, 2% by weight to 20% by weight based on the total amount of the photosensitive resin composition. When the acrylic binder resin is contained within the above range, the color filter is excellent in developability in the production of a color filter, and the cross-linkability is improved, whereby an excellent surface smoothness can be obtained.

Photopolymerization  Monomer

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

Since the photopolymerizable monomer has the ethylenically unsaturated double bond, sufficient polymerization is caused during exposure in the pattern formation step, whereby a pattern having excellent heat resistance, light resistance and chemical resistance can be formed.

Specific examples of the photopolymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol Acrylate such as di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (Meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di Acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol There may be mentioned furnace methyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolak epoxy (meth) acrylate, and the like.

A commercially available product of the photopolymerizable monomer is exemplified as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ^®, the same M-111 ^®, the same M-114 ^®; KAYARAD TC-110S ^® and TC-120S ^{® from} Nihon Kayaku Co., Ltd.; Osaka yukki the like Kagaku Kogyo (main)社of ^{V-158 ®, V-2311} ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ^®, copper or the like M-240 ^®, the same M-6200 ^®; KAYARAD HDDA ^® , HX-220 ^® and R-604 ^{® from} Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of ^{社V-260 ®, V-} 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ^®, the same M-400 ^®, the same M-405 ^®, the same M-450 ^®, Dong M -7100 ^® , copper M-8030 ^® , copper M-8060 ^® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ^®, copper DPCA-20 ^{®, ®} copper -30, -60 ^® copper, copper ^® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ^®, copper ^® -300, -360 ^® copper, copper -GPT ^®, copper -3PA ^®, and the like copper -400 ^®. These products may be used alone or in combination of two or more.

The photopolymerizable monomer may be treated with an acid anhydride to give better developing properties.

The photopolymerizable monomer may be contained in an amount of 1 wt% to 20 wt% based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is contained within the above range, the photopolymerizable monomer sufficiently cures upon exposure in the pattern formation step, is excellent in reliability, and is excellent in developability in an alkaline developer.

Light curing Initiator

The photopolymerization initiator may be an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an oxime-based compound.

Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.

Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho- (Trichloromethyl) -s-triazine, 2, 4-methoxynaphtho-1-yl) -4,6-bis 6-triazine, trichloromethyl (piperonyl) -6-triazine and 2,3,4-trichloromethyl (4'-methoxystyryl) -6-triazine.

Examples of the oxime compounds include 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (o- Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone.

The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.

The photopolymerization initiator may be contained in an amount of 0.1% by weight to 10% by weight based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, photopolymerization sufficiently occurs upon exposure in the pattern formation step, and the decrease of the transmittance due to the unreacted initiator can be prevented.

menstruum

The solvent may be a material that has compatibility with the colorant, the acrylic binder resin, the photopolymerizable monomer, and the photopolymerization initiator but does not react with the photopolymerizable monomer.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Hydroxyacetic acid alkyl esters such as methylhydroxyacetate, ethylhydroxyacetate and butylhydroxyacetate; Alkoxyalkyl esters such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate and propyl 2-hydroxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-hydroxy-2-methylpropionic acid alkyl esters such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate and methyl 2-hydroxy-3-methyl butanoate; Or ethyl pyruvate. Examples of the ketone acid esters include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide Benzyl alcohol, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, Ethyl benzoate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. These may be used alone or in combination of two or more.

In view of the miscibility and reactivity of the solvent, glycol ethers such as ethylene glycol monoethyl ether and the like; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxyethyl propionate; Diethylene glycol such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

The solvent may be contained in an amount of from about 20% by weight to about 90% by weight based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the coating property of the photosensitive resin composition is excellent and excellent flatness can be maintained.

Other additives

The above-mentioned photosensitive resin composition may contain at least one selected from the group consisting of malonic acid, malonic acid, and malonic acid, in order to prevent spots and spots upon application, to improve the leveling performance, 3-amino-1,2-propanediol; A silane-based coupling agent comprising a vinyl group or (meth) acryloxy group; Leveling agents; Fluorine surfactants; A radical polymerization initiator, and the like.

The above-mentioned photosensitive resin composition may further contain an additive such as an epoxy compound in order to improve the adhesion with the substrate.

Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The content of the additive can be easily adjusted according to desired properties.

Another embodiment provides a color filter manufactured using the above-described photosensitive resin composition. A method of manufacturing the color filter is as follows.

The above-mentioned photosensitive resin composition for a color filter is applied on a glass substrate to which nothing is applied, or on a glass substrate on which a protective film of SiNx is applied in a thickness of 500 Å to 1500 Å, using a suitable method such as spin coating or slit coating To a thickness of 3.1 mu m to 3.4 mu m, respectively. After the application, light is irradiated to form a pattern necessary for the color filter. After the light is irradiated and the coating layer is treated with an alkali developing solution, the unexposed portions of the coating layer are dissolved and a pattern necessary for the color filter is formed. By repeating this process according to the required number of R, G, and B colors, a color filter having a desired pattern can be obtained.

In addition, in the above process, the image pattern obtained by development may be further heated or cured by actinic ray irradiation or the like to further improve crack resistance, solvent resistance, and the like.

Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only a preferred embodiment of the present invention, and the present invention is not limited by the following examples.

(Compound synthesis)

( Acrylate group  Containing dyes)

Synthetic example  One

[Synthesis of Compound (3-1)] [

To the flask equipped with a stirrer was added 735 ml of methylene chloride, and the mixture was cooled to 0 ° C in a nitrogen stream, and 85 g (147 mmol) of Sulforhodamine B acid chloride was added thereto and stirred. Then, 29.2 g (177 mmol) of 2-aminoethyl methacrylate hydrochloride, 0.899 g (7.37 mmol) of N, N-dimethylaminopyridine and 38.3 g (53 ml, 295 mmol) of triethylamine were further added And stirred at room temperature for 15 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 65.9 g (yield 67%) of a compound represented by the following formula (3-1).

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.67 (s, 1H), 8.13 (dd, 1H), 7.52 (d, 1H), 7.17-6.95 (m, 6H), 6.18 (s, 1H), 2H), 1.96 (s, 3H), 1.34-1. 30 (m, 12H)

Synthetic example  2

3-4 Synthesis method

To the flask equipped with a stirrer was added 735 ml of methylene chloride, and the mixture was cooled to 0 ° C in a nitrogen stream, and 85 g (147 mmol) of Sulforhodamine B acid chloride was added thereto and stirred. Thereafter, 18.6 g (177 mmol) of 2-aminoethyl 2-2 (aminoethoxy) ethanol and 0.899 g (7.37 mmol) of N, N-dimethylaminopyridine, 38.3 g (53 ml, 295 mmol) was further added, and the mixture was stirred at room temperature for 15 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate and dried. To the solid was added 735 ml of methylene chloride. The mixture was cooled to 0 ° C under a nitrogen stream and stirred. 18.5 g (177 mmol) of methacryloyl chloride and 17.9 g (177 mmol) of triethylamine were added to the mixture, followed by stirring at room temperature for 5 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 72 g (yield 62%) of a compound represented by the following formula 3-4.

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.67 (s, 1H), 8.17 (dd, 1H), 7.55 (d, 1H), 7.14-6.96 (m, 6H), 6.16 (s, 1H), (M, 2H), 1.95 (s, 3H), 3.63-3.53 (m, 2H) ), 1.32-1.28 (m, 12H)

Synthetic example  3

[Chemical Formulas 3-6 Synthesis Method]

To the flask equipped with a stirrer was added 735 ml of methylene chloride, and the mixture was cooled to 0 ° C in a nitrogen stream, and 85 g (147 mmol) of Sulforhodamine B acid chloride was added thereto and stirred. Thereafter, 20.4 g (177 mmol) of 2-aminoethyl trans-4-aminocyclohexanol, 0.899 g (7.37 mmol) of N, N-dimethylaminopyridine and 38.3 g (53 ml, 295 mmol ) Was further added, and the mixture was stirred at room temperature for 15 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate and dried. To the solid was added 735 ml of methylene chloride. The mixture was cooled to 0 ° C under a nitrogen stream and stirred. 18.5 g (177 mmol) of methacryloyl chloride and 17.9 g (177 mmol) of triethylamine were added to the mixture, followed by stirring at room temperature for 5 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 74 g (yield 63%) of a compound represented by the following Chemical Formula 3-6.

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.65 (s, 1H), 8.12 (dd, 1H), 7.52 (d, 1H), 7.19-6.97 (m, 6H), 6.16 (s, 1H), 2H), 1.66 (t, 2H), 1.64 (t, 2H), 1.64 (s, , 1.33-1.29 (m, 12H)

Synthetic example  4

[Chemical Formula 3-8 Synthetic Method]

To the flask equipped with a stirrer was added 735 ml of methylene chloride, and the mixture was cooled to 0 ° C in a nitrogen stream, and 85 g (147 mmol) of Sulforhodamine B acid chloride was added thereto and stirred. Thereafter, 10.8 g (177 mmol) of 2-aminoethyl 2-aminoethanol, 0.899 g (7.37 mmol) of N, N-dimethylaminopyridine and 38.3 g (53 ml, 295 mmol) of triethylamine were added thereto, Lt; / RTI > for 15 h. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate and dried. To the solid was added 735 ml of methylene chloride. The mixture was cooled to 0 ° C under a nitrogen stream and stirred. 27.5 g (177 mmol) of 2-isocyanatoethyl methacrylate and 1.1 g (1.7 mmol) of dibutyltin dilaurate were added to the mixture, followed by stirring at room temperature for 5 hours . Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 80 g (yield 70%) of a compound represented by the following Chemical Formula 3-8.

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.68 (s, 1H), 8.14 (dd, 1H), 7.53 (d, 1H), 7.16-6.94 (m, 6H), 6.17 (s, 1H), (M, 2H), 1.94 (m, 2H), 1.94 (m, 2H) s, 3H), 1.35-1.31 (m, 12H)

Synthetic example  5

[Synthesis of Compound (3-11)] [

735 ml of dimethylformamide was added to the flask containing the stirrer, and the mixture was cooled at 0 캜 under a nitrogen stream, and 98.5 g (147 mmol) of the red solid of the above formula (3-1) was added and stirred. Thereafter, 101.6 g (735 mmol) of potassium carbonate and 34.2 g (177 mmol) of 2-bromoethyl methacrylate were further added and the mixture was stirred at room temperature for 15 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 72.9 g (yield 73%) of a compound represented by the following formula.

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.67 (s, 1H), 8.13 (dd, 1H), 7.52 (d, 1H), 7.17-6.95 (m, 6H), 6.17 (s, 2H), 2H), 4.17 (t, 4H), 3.74-3.64 (m, 16H), 3.41-3.37 (m, 4H)

( Amine group  Containing dyes)

Synthetic example  6

[Synthesis method 4]

250 ml of methylene chloride was added to the flask equipped with a stirrer, and the mixture was cooled to 0 占 폚 under a nitrogen stream, and 2.5 g (41.6 mmol) of ethylenediamine, 1.4 g (13.9 mmol) of triethylamine and 0.25 g And the mixture was stirred. 8 g (13.9 mmol) of Sulforhodamine B acid chloride was added dropwise to the mixture over 2 hours, and the mixture was stirred at room temperature for 15 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 6.7 g (yield 81%) of a compound represented by the following formula 4-1.

[NMR data]

¹ H NMR (300 MHz, CD ₃ OD):? = 8.67 (s, IH), 8.17 (d, IH), 7.58 (d, IH), 7.14-6.96 (M, 4H), 1.40-1.15 (m, 12H), 5.66 (s,

(A dye containing an isocyanate group)

Synthetic example  7

[Synthesis method of Chemical formula 5-1]

735 ml of ethyl acetate was added to the flask containing the stirrer, and the mixture was cooled at 0 캜 under a nitrogen stream, and 86.1 g (147 mmol) of the solid of the formula 4-1 was added and stirred. 52.5 g (177 mmol) of triphosgene was further added thereto, and the mixture was refluxed for 4 hours and stirred. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 70.9 g (yield 75%) of a compound represented by the following formula 5-1.

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.68 (s, 1H), 8.16 (d, 1H), 7.58 (d, 1H), 7.15-6.94 (m, 6H), 4.18 (t, 1H), 3H), 3.73-3.66 (m, 8H), 3.54-2.99 (m, 4H), 1.42-1.17 (m, 12H)

( Alcoholic  Containing dyes)

Synthetic example  8

[Synthesis of Compound (6-1)

To the flask equipped with a stirrer was added 735 ml of methylene chloride, and the mixture was cooled to 0 ° C in a nitrogen stream, and 85 g (147 mmol) of Sulforhodamine B acid chloride was added thereto and stirred. Then, 10.8 g (177 mmol) of 2-aminoethyl 2-aminoethanol, 0.899 g (7.37 mmol) of N, N-dimethylaminopyridine and 38.3 g (53 ml, 295 mmol) of triethylamine were further added thereto, Lt; / RTI > for 15 h. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 63.5 g (65% yield) of a compound represented by the following formula (3-1).

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.67 (s, 1H), 8.16 (d, 1H), 7.58 (d, 1H), 7.13-6.92 (m, 6H), 4.2 (t, 1H), 3H), 3.73-3.66 (m, 8H), 3.52-2.97 (m, 4H), 1.42-1.17 (m, 12H)

Synthetic example  9

[Synthesis method of formula 6-4]

To the flask equipped with a stirrer was added 735 ml of methylene chloride, and the mixture was cooled to 0 ° C in a nitrogen stream, and 85 g (147 mmol) of Sulforhodamine B acid chloride was added thereto and stirred. Thereafter, 16.1 g (177 mmol) of serinol, 0.899 g (7.37 mmol) of N, N-dimethylaminopyridine and 38.3 g (53 ml, 295 mmol) of triethylamine were further added and the mixture was stirred at room temperature for 15 hours. Thereafter, the mixture was concentrated under reduced pressure using a rotary evaporator, and the resulting red solid was washed with ethyl acetate to obtain 70.1.5 g (yield 69%) of a compound represented by the following formula 6-4.

[NMR data]

_{^{1 H NMR (300MHz, CD 3}} OD): δ = 8.67 (s, 1H), 8.16 (d, 1H), 7.58 (d, 1H), 7.13-6.92 (m, 6H), 4.2 (t, 1H), 3.73-3.66 (m, 8H), 3.50-2.95 (m, 5H), 1.42-1.17 (m, 12H)

( Polymer  synthesis)

(acryl Polymer )

Synthetic example  13

[Acrylic polymer synthesis method and molecular weight]

100 ml of methyl ethyl ketone was added to a flask equipped with a stirrer, and 3 g (4.6 mmol) of the solid of the formula 3-1, 7 g (37.9 mmol) of 2-ethylhexyl acrylate and 0.3 g (1.8 ml) of azobisisobutyronitrile mmol) were added and mixed and stirred at 80 DEG C for 15 hours to obtain a copolymer.

Polystyrene equivalent average molecular weight: number average molecular weight (Mn) = 2,100, weight average molecular weight (Mw) = 3,000

( Urea Polymer )

Synthetic example  14

[Synthesis of urea polymer and molecular weight]

100 ml of methyl ethyl ketone was added to a flask equipped with a stirrer, and 6.7 g (40 mmole) of hexamethylene diisocyanate, 3.5 g (30 mmole) of 1,6-hexanediol and 0.01 g (0.02 mmole) of dibutyltin dilaurate mmol) were added and mixed and stirred at 80 ° C for 15 hours. Then, 10.9 g (20 mmol) of the solid of the formula 4-1 was added to the mixture, followed by stirring and mixing at 80 DEG C for 1 hour to obtain a copolymer.

Polystyrene equivalent average molecular weight: number average molecular weight (Mn) = 2,100, weight average molecular weight (Mw) = 3,400

(urethane Polymer )

Synthetic example  15

[Urethane polymer synthesis method and molecular weight]

100 ml of methyl ethyl ketone was added to a flask equipped with a stirrer, and 5.0 g (30 mmol) of hexamethylene diisocyanate, 4.7 g (40 mmol) of 1,6-hexanediol, and 0.01 g mmol) were added and mixed and stirred at 80 ° C for 15 hours. Then, 12.2 g (20 mmol) of the solid of the formula 5-1 was added to the mixture, followed by mixing and stirring at 80 ° C for 1 hour to obtain a copolymer.

Polystyrene equivalent average molecular weight: number average molecular weight (Mn) = 2,200, weight average molecular weight (Mw) = 3,300

Evaluation 1: Measurement of solubility

(PGMEA, Anone, MeOH) was added to 0.5 g of the compound represented by the general formula (3-1) and the compound represented by the general formula (7-1), and the solution was stirred at 25 ° C. and 100 ° C. in a mix rotor (MIXROTAR VMR- After stirring for 1 hour at rpm, the dissolution state (content of dissolved compound) of the compound was confirmed, and the results are shown in Table 1 below.

Content of dissolved compound (% by weight) compound Dilution solvent (PGMEA) Dilution solvent (Anone) Dilution solvent (MeOH) 0.1 or less 0.1 or less 0.1 to 0.5 3-1 0.1 3.0 10.0 or higher 7-1

Evaluation 2: Measurement of permeability

The concentration of each of the compounds represented by Formulas (3-1), (6-3), (7-1), (7-2) and (8-1) was 0.001% by weight or less by using cyclohexanol in a 10.00 mm thick quartz cell. Was measured by UV / VIS Spectrophotometer: UV-1800 (SHIMADZU, Inc.) at a wavelength of 200 nm to 800 nm, and the results are shown in FIGS. 1 to 5.

From Table 1 and FIGS. 1 to 5, it can be confirmed that the compounds of the present invention all have excellent solubility and spectroscopic characteristics.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.

Claims (12)

A polymer formed by a copolymerization reaction between a compound represented by the following formula (1) and a monomer selected from the group consisting of ethylenically unsaturated monomers, isocyanate monomers, alcohol monomers and combinations thereof:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (2), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (2)
(2)

In Formula 2,
L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,
X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,
Y is a single bond, -O-, -C (═O) -, -C (═O) R'-, -OR "-, -R" O- or -OC -, wherein R 'to R'"each independently represent a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group or a substituted or unsubstituted C6 to C20 arylene group,
Z is a substituted or unsubstituted acrylate group, a substituted or unsubstituted amine group, an isocyanate group, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group or -OC (= O) R ''''''Is a substituted or unsubstituted C1 to C20 alkyl group,
n is an integer of 1 or 2;
(Wherein "substituted" to "substituted" it means one or more hydrogen atom is a halogen atom (F in the functional group of the present invention, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amine group (NH _2, NH ( R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, a hydrazine group, a hydrazide A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, Substituted heteroaryl group " means a group substituted with at least one substituent selected from the group consisting of < RTI ID = 0.0 >
The method according to claim 1,
Wherein R ⁵ and R ⁶ are both represented by the general formula (2).
The method according to claim 1,
Wherein the polymer is an acrylic polymer,
Wherein the acrylic polymer is a polymer formed by a copolymerization reaction between a compound represented by the following formula (1) and an ethylenically unsaturated monomer:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (3), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (3)
(3)

In Formula 3,
L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,
X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,
Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group, An unsubstituted C3 to C20 cycloalkylene group,
R ⁹ is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
n1 is an integer of 1 or 2;
(Wherein "substituted" to "substituted" it means one or more hydrogen atom is a halogen atom (F in the functional group of the present invention, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amine group (NH _2, NH ( R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, a hydrazine group, a hydrazide A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, Substituted heteroaryl group " means a group substituted with at least one substituent selected from the group consisting of < RTI ID = 0.0 >
The method of claim 3,
Wherein said ethylenically unsaturated monomer is at least one selected from the group consisting of an aromatic vinyl compound, an unsaturated carboxylic acid ester compound, an unsaturated carboxylic acid aminoalkyl ester compound, a carboxylic acid vinyl ester compound, an unsaturated carboxylic acid glycidyl ester compound, a vinyl cyanide compound, an unsaturated amide compound, The polymer is any one selected.
The method according to claim 1,
The polymer is an urea polymer,
Wherein the urea polymer is a polymer formed by a copolymerization reaction between a compound represented by the following formula (1) and an isocyanate monomer:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula 4, provided that at least one of R ⁵ and R ⁶ is represented by the following formula 4,
[Chemical Formula 4]

In Formula 4,
L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,
X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,
Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,
R ¹⁰ and R ¹¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
n2 is an integer of 1 or 2;
(Wherein "substituted" to "substituted" it means one or more hydrogen atom is a halogen atom (F in the functional group of the present invention, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amine group (NH _2, NH ( R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, a hydrazine group, a hydrazide A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, Substituted heteroaryl group " means a group substituted with at least one substituent selected from the group consisting of < RTI ID = 0.0 >
The method according to claim 1,
Wherein the polymer is a urethane polymer,
The urethane polymer is a polymer formed by a copolymerization reaction of a compound represented by the following formula (1) and an alcohol monomer:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (5), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (5)
[Chemical Formula 5]

In Formula 5,
L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,
X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,
Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,
n3 is an integer of 1 or 2;
(Wherein "substituted" to "substituted" it means one or more hydrogen atom is a halogen atom (F in the functional group of the present invention, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amine group (NH _2, NH ( R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, a hydrazine group, a hydrazide A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, Substituted heteroaryl group " means a group substituted with at least one substituent selected from the group consisting of < RTI ID = 0.0 >
The method according to claim 1,
Wherein the polymer is a urethane polymer,
The urethane polymer is a polymer formed by copolymerization reaction of a compound represented by the following formula (1) with an isocyanate monomer:
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
R ⁵ and R ⁶ are each independently a hydrogen atom or a group represented by the following formula (6), provided that at least one of R ⁵ and R ⁶ is represented by the following formula (6)
[Chemical Formula 6]

In Formula 6,
L is a single bond, a divalent aliphatic organic group or a trivalent aliphatic organic group,
X is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C3 to C20 cycloalkylene group,
Y is a single bond, -OR "'- or -OC (═O) NHR'" -, and R "and R '" are each independently a substituted or unsubstituted C1 to C20 alkylene group or a substituted or non- An unsubstituted C3 to C20 cycloalkylene group,
n4 is an integer of 1 or 2;
(Wherein "substituted" to "substituted" it means one or more hydrogen atom is a halogen atom (F in the functional group of the present invention, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amine group (NH _2, NH ( R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, a hydrazine group, a hydrazide A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, Substituted heteroaryl group " means a group substituted with at least one substituent selected from the group consisting of < RTI ID = 0.0 >
The method according to claim 1,
(2) is a compound represented by any one of the following formulas (7) to (10):
(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above Chemical Formulas 7 to 10,
L is a single bond, a divalent or trivalent aliphatic organic group, or a divalent or trivalent alicyclic organic group,
R ^a to R ^g are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
n5 is an integer of 1 or 2,
m1 to m4 and m6 are each independently an integer of 0 to 15,
m5 is an integer of 1 to 5;
A colorant comprising the polymer of any one of claims 1 to 8.
A photosensitive resin composition comprising the colorant of claim 9.
11. The method of claim 10,
Wherein the photosensitive resin composition further comprises a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.
A color filter produced from the photosensitive resin composition of claim 11.

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