KR102306981B1 - Xanthene-based compound, color material composition comprising the same, photosensitive resin composition, photoresist, color filter, and display device - Google Patents

Abstract

The present specification relates to a compound represented by Formula 1 and a color material composition comprising the same, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.

Description

Xanthene-based compound, color material composition comprising the same, photosensitive resin composition, photosensitive material, color filter, and display device

The present specification relates to a xanthene-based compound, a color material composition comprising the same, and a photosensitive resin composition. In addition, the present specification relates to a photosensitive material manufactured using the photosensitive resin composition, a color filter, and a display device including the same.

In recent color filters, performance characterized by high luminance and high contrast ratio is required. In addition, one of the main purposes of the development of the display device is to differentiate the performance of the display device through the improvement of color purity and to improve the productivity in the manufacturing process.

Since the pigment type used as a color material for a color filter is present in the color photoresist in a particle-dispersed state, it is difficult to control the luminance and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, they are agglomerated in the color filter, resulting in poor dissolution and dispersibility, and multiple scattering of light occurs due to large aggregated particles. The scattering of such polarized light is pointed out as the main factor for lowering the contrast ratio. Efforts to improve luminance and contrast ratio through ultra-fine pigmentation and dispersion stabilization are continuing, but the degree of freedom in selecting color materials for realizing color coordinates for high-color purity display devices is limited. In addition, the previously developed color material, particularly the pigment dispersion method using a pigment, has reached its limit in improving the color purity, luminance, and contrast ratio of a color filter using the same.

Accordingly, there is a demand for the development of a new color material capable of improving color reproduction, luminance, and contrast ratio by increasing color purity.

Korean Patent Publication No. 2001-0009058

An object of the present specification is to provide a xanthene-based compound having a novel structure, a color material composition including the same, a photosensitive resin composition, a photosensitive material manufactured using the same, a color filter, and a display device including the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 and L2 are the same as or different from each other, and each independently a direct bond; -L'-OCO-L''; Or a substituted or unsubstituted alkylene group,

The L' and L'' are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group,

A1 and A2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group,

B1 and B2 are the same as or different from each other, and each independently hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R1 to R3 are the same as or different from each other, and each independently hydrogen; sulfonamide group; or a sulfonate group,

r1 is an integer of 1 to 5, and when r1 is 2 or more, R1 of 2 or more are the same as or different from each other,

r2 and r3 are integers from 0 to 3, and when r2 and r3 are 2 or more, the structures in parentheses are the same as or different from each other,

X is an anionic group,

a is an integer of 0 or 1.

Another exemplary embodiment of the present specification provides a color material composition comprising the compound represented by Formula 1, and further comprising at least one of a dye and a pigment.

Another exemplary embodiment of the present specification is a compound represented by Formula 1; binder resin; polyfunctional monomers; photoinitiators; And it provides a photosensitive resin composition comprising a solvent.

Another exemplary embodiment of the present specification provides a photosensitive material prepared using the photosensitive resin composition.

An exemplary embodiment of the present specification provides a color filter including the photosensitive material.

An exemplary embodiment of the present specification provides a display device including the color filter.

The compound according to an exemplary embodiment of the present specification may be used as a color material in the photosensitive resin composition, and in particular, by using the compound, a red color filter having high brightness and high heat resistance may be manufactured.

Hereinafter, the present specification will be described in more detail.

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

According to an exemplary embodiment of the present specification, there is provided a compound represented by Formula 1 above.

C.I. Rhodamine dyes such as Acid Red 52, Rhodamine B, and 6G are widely used as red or violet dyes. The rhodamine dye exemplified above is bright and has excellent color development, but lacks heat resistance and has a strong fluorescence intensity, so that when applied as a dye for a color filter, the contrast ratio is insufficient.

Accordingly, the present invention improves the heat resistance of a material by introducing an electron withdrawing group into the xanthene structure, and electrons in the material go through a meta-stabilized state to decrease the fluorescence intensity without going directly to the ground state from the excited state. An electro withdrawing group was introduced. As a result of the introduction, it was confirmed that the fluorescence intensity decreased.

Examples of the substituents of the compound represented by Formula 1 are described below, but are not limited thereto.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

refers to a site bonded to another substituent or a bonding group.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; carboxyl group; imid; amide group; anionic group; alkoxy group; sulfonamide group; sulfonate group; an alkyl group; cycloalkyl group; alkenyl group; cycloalkenyl group; sulfonate group; amine group; aryl group; heteroaryl group; silyl group; an alkyl sulfoxy group; arylsulfoxy group; boron group; acryloyl group; acrylate group; ether group; It means that it is substituted with one or more substituents selected from the group comprising a heterocyclic group and an anionic group containing at least one of N, O, S or P atoms or does not have any substituents.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox tyl group, etc., but are not limited thereto. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and particularly preferably a cyclopentyl group or a cyclohexyl group, but is not limited thereto. .

In the present specification, the alkylene group means that there are two bonding sites in an alkane. The alkylene group may be linear, branched or cyclic. The number of carbon atoms in the alkylene group is not particularly limited, but is, for example, 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, and more specifically 1 to 10 carbon atoms.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, an acridyl group, a pyridazine group , quinolinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran group and the like, but is not limited thereto.

In the present specification, the description of the above-mentioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the sulfide group may be represented by -SR'''. Wherein R''' is a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.

In the present specification, the sulfonamide group may be represented by _{-SO 2 NM1M2.} M1 and M2 are the same as or different from each other, and each independently an alkyl group; cycloalkyl group; aryl group; Or it may be a heteroaryl group, but is not limited thereto.

In the present specification, the sulfonate group may be represented by _{-SO 3 M.} The -SO ₃ M may _{mean that -SO 3} ^- and M are ionic bonds or salt bonds. M may correspond to a group 1 element of the periodic table. The group 1 element of the periodic table is, for example, Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; It ^{may be Fr +} , but is not limited thereto.

In the present specification, the anionic group has a chemical bond with the structure of Formula 1, and the anionic group is not particularly limited, for example, US Patent No. 7,939,644, Japanese Patent Application Laid-Open No. 2006-003080, Japanese Patent Application Laid-Open No. 2006-001917 , Japanese Patent Application Laid-Open No. 2005-159926, Japanese Patent Application Laid-Open No. 2007-7028897, Japanese Patent Application Laid-Open No. 2005-071680, Korean Patent Application Laid-Open No. 2007-7000693, Japanese Patent Application Laid-Open No. 2005-111696, Japanese Patent Application Laid-Open No. 2008-249663, Anions described in Japanese Patent Application Laid-Open No. 2014-199436 can be applied. Specific examples of the anionic group include trifluoromethanesulfonic acid anion, bis(trifluoromethylsulfonyl)amide anion, bis(trifluoromethylsulfonyl)imide anion, bistrifluoromethanesulfonimide anion, bis Perfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis(4-fluorophenyl)borate, tetrakis(pentafluorophenyl)borate, tristrifluoromethanesulfonylmethide, SO ₃ ^- , CO ₂ ^- , SO ₂ N ^- SO ₂ CF ₃ , SO ₂ N ^- SO ₂ CF ₂ CF ₃ , SO ₂ N ^- SO ₂ C ₆ H _{5 , a} halogen group such as a fluorine group, an iodine group, a chlorine group, etc., but only this It is not limited.

In the present specification, the anionic group may have an anion itself, or may exist in the form of a complex compound with other cations. Accordingly, the sum of the total charges of the compound molecules of the present invention may vary depending on the number of substituted anionic groups. Since the compound of the present invention has a cation in one amine group, the sum of the total charges of the molecule may have a value ranging from an anion to 0 as much as a value obtained by subtracting 1 from the number of substituted anionic groups.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; -L'-OCO-L''; or a substituted or unsubstituted alkylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; -L'-OCO-L''; or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; -L'-OCO-L''; or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; -L'-OCO-L''; or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L1 is a direct bond; -L'-OCO-L''; a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; Or a substituted or unsubstituted propylene group.

In one embodiment of the present specification, L1 is a direct bond; -L'-OCO-L''; methylene group; ethylene group; or a propylene group.

In one embodiment of the present specification, L2 is -L'-OCO-L''; or a substituted or unsubstituted ethylene group.

In one embodiment of the present specification, L2 is -L'-OCO-L''; or an ethylene group.

In an exemplary embodiment of the present specification, L' and L'' are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted alkylene group.

In an exemplary embodiment of the present specification, L' and L'' are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L' and L'' are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L' and L'' are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, L' and L'' are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted methylene group; or a substituted or unsubstituted ethylene group.

In an exemplary embodiment of the present specification, L' is an ethylene group.

In one embodiment of the present specification, L'' is a direct bond; methylene group; or an ethylene group.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted ethyl group.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents an ethyl group.

In an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In an exemplary embodiment of the present specification, B1 is hydrogen; hydroxyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, B1 is hydrogen; hydroxyl group; methyl group; a methyl group substituted with a thiophene group; ethyl group; an ethyl group substituted with a sulfide group; Or a nitro group, fluorine, chlorine, methoxy group, -SO ₂ CF ₃ ; or a phenyl group substituted with _{-CF 3 .}

In an exemplary embodiment of the present specification, B1 is hydrogen; hydroxyl group; methyl group; a methyl group substituted with a thiophene group; ethyl group; -SCH ₃ substituted ethyl group; Or a nitro group, fluorine, chlorine, a methoxy group (-OCH ₃ ), -SO ₂ CF ₃ ; or a phenyl group substituted with _{-CF 3 .}

In an exemplary embodiment of the present specification, B2 is a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, B2 is a methyl group substituted with a thiophene group; -SCH ₃ substituted ethyl group; Or a nitro group, a nitrile group, fluorine, chlorine, a methoxy group (-OCH ₃ ), -SO ₂ CF ₃ ; Or a phenyl group substituted with _{-CF 3 .}

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; sulfonamide group; sulfonate group; or an anionic group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or -SO ₂ N ^-, and SO ₂ C ₆ H _5, wherein M1 and M2 are the same as or different from each other and each independently represent a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or -SO ₂ N ^- is SO ₂ C ₆ H _5, and wherein M1 and M2 are the same as or different from each other and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or -SO ₂ N ^- is SO ₂ C ₆ H _5, and wherein M1 and M2 are the same as or different from each other and each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or -SO ₂ N ^- is SO ₂ C ₆ H _5, and wherein M1 and M2 are the same as or different from each other and each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or ^{_{-SO 2 N - SO 2 C 6}} H 5 , and wherein M1 and M2 are the same as or different from each other and each independently represent a substituted or unsubstituted ethyl group; or a substituted or unsubstituted hexyl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or ^{_{-SO 2 N - SO 2 C 6}} H 5 , and wherein M1 and M2 are the same or different and each independently represents a group with one another; or an n-hexyl group.

In an exemplary embodiment of the present specification, R1 is hydrogen; -SO ₂ NM1M2; -SO ₃ ^- ; Or ^{_{-SO 2 N - SO 2 C 6}} H 5 , and wherein M1 and M2 are the same or different and each independently represents a group with one another; or an n-hexyl group.

In an exemplary embodiment of the present specification, R2 is hydrogen.

In an exemplary embodiment of the present specification, R3 is hydrogen.

In an exemplary embodiment of the present specification, r1 is an integer of 1 to 5, when r1 is 2 or more, 2 or more R1 are the same as or different from each other, r2 and r3 are integers from 0 to 3, r2 and r3 are 2 In the above case, the structures in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, X is an anionic group.

In an exemplary embodiment of the present specification, X is a bis(trifluoromethylsulfonyl)imide or trifluoromethanesulfonic acid anion.

In one embodiment of the present specification, a is an integer of 0 or 1.

In one embodiment of the present specification, a is 0.

In one embodiment of the present specification, a is 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following structures, and the following structures represent isomers of Chemical Formula 1, and Chemical Formula 1 represents a representative structure. Isomer means molecules having the same molecular formula but different physical/chemical properties.

In the above structure, the substituents are as defined in Formula 1 above.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

L1, A1, A2, B1, R1 to R3, r1 to r3, X and a are as defined in Formula 1 above,

L3 is a substituted or unsubstituted alkylene group,

B3 is a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, L3 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L3 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L3 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, L3 is a substituted or unsubstituted ethylene group.

In an exemplary embodiment of the present specification, L3 is an ethylene group.

In an exemplary embodiment of the present specification, B3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, B3 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, B3 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In an exemplary embodiment of the present specification, B3 is a methyl group substituted with a thiophene group; -SCH ₃ substituted ethyl group; Or a nitro group, a nitrile group, fluorine, chlorine, a methoxy group (-OCH ₃ ), -SO ₂ CF ₃ ; Or a phenyl group substituted with _{-CF 3 .}

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 3 below.

[Formula 3]

In Formula 3,

A1, A2, R1 to R3, r1 to r3, X and a are as defined in Formula 1 above,

L3 and L4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group,

B3 and B4 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, the definition of B4 is the same as the definition of B3.

In one embodiment of the present specification, the definition of l4 is the same as the definition of l3.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas, but is not necessarily limited thereto.

An exemplary embodiment of the present specification provides a color material composition including the compound and further comprising at least one of a dye and a pigment.

An exemplary embodiment of the present specification is that the dye is a xanthene-based dye, a cyanine-based dye, an anthraquinone-based dye, a porphyrin-based dye, a triarylmethane-based dye, an azo metal complex, a coumarin-based dye, an azo-based dye, and a quinophthalone-based dye It is one or more dyes selected from, and the pigment provides a color material composition that is a blue pigment, a purple pigment, or a yellow pigment.

Specifically, the dye may be a metal complex of Orasol Red 330, Solvent Orange 45, Solvent Orange 54, and Solvent Orange 62, but is not limited thereto.

The color material composition may include only the compound of Formula 1, but includes the compound of Formula 1 and one or more of the aforementioned dyes, or includes the compound of Formula 1 and one or more of the aforementioned pigments, or , one or more of the aforementioned dyes and one or more of the aforementioned pigments.

According to an exemplary embodiment of the present specification, a photosensitive resin composition including the color material composition may be provided.

According to an exemplary embodiment of the present specification, the photosensitive resin composition may include a compound represented by Formula 1; binder resin; polyfunctional monomers; photoinitiators; and a solvent.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of the photosensitive resin composition.

The binder resin may use a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.

The polyfunctional monomer imparting the mechanical strength of the membrane is an unsaturated carboxylic acid ester; aromatic vinyls; unsaturated ethers; unsaturated imides; and an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl ( meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydropuffril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) ) acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only It is not limited.

Specific examples of the aromatic vinyl include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, but is not limited thereto.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. may be, but is not limited thereto.

Examples of the acid anhydride include, but are not limited to, maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride, and the like.

The monomer imparting alkali solubility is not particularly limited as long as it contains an acid group, and for example, (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, ω-carboxy polycaprolactone mono(meth)acrylate selected from the group consisting of It is preferable to use one or more types, but is not limited thereto.

According to an exemplary embodiment of the present specification, the binder resin has an acid value of 50 to 130 KOH mg/g, and a weight average molecular weight of 1,000 to 50,000.

The polyfunctional monomer is a monomer that forms a photoresist image by light, specifically propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethyl Propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate, glycidyl methacrylate , may be one or a mixture of two or more selected from the group consisting of epoxycyclohexyl methacrylate.

The photoinitiator is not particularly limited as long as it is an initiator that triggers crosslinking by generating radicals by light, for example, selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. There may be more than one type.

The acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoinmethyl ether, benzoinethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and the like.

As the biimidazole-based compound, 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4 ,4',5,5'-tetrakis (3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl)-4, 4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , but not limited thereto.

The triazine-based compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionate, ethyl-2-{4-[2,4 -bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6 -yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine-6 -yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionamide, 2,4-bis(trichloro methyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl-s -triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.

The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigisa, SI 124), ethanone, -1- (9 -ethyl)-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime) (CGI 242), N-1919 (Adecas), and the like, but is not limited thereto.

The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy It may be at least one selected from the group consisting of propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is not limited thereto.

According to an exemplary embodiment of the present specification, based on the total weight of the solid content in the photosensitive resin composition, the content of the compound represented by Formula 1 is 5% to 60% by weight, and the content of the binder resin is 1% by weight to 60 wt%, the content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional monomer is 0.1 wt% to 50 wt%.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the photosensitive resin composition. The solid content and the basis of weight % based on the solid content of each component may be measured by general analytical means used in the art, such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the photosensitive resin composition may further include an antioxidant.

According to an exemplary embodiment of the present specification, the content of the antioxidant is 0.1 wt% to 20 wt% based on the total weight of the solid content in the photosensitive resin composition.

According to an exemplary embodiment of the present specification, the photosensitive resin composition includes one or two or more additives selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersing agent, and a leveling agent. additionally include

According to an exemplary embodiment of the present specification, the content of the additive is 0.1 wt% to 20 wt% based on the total weight of solids in the photosensitive resin composition.

The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; fluorenone compounds such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type, such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, diisopropyl thioxanthone compound; xanthone-based compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. acridine-based compounds; dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, and 9,10-phenanthrenequinone; phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo coumarin-based compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.

The curing accelerator is used to increase curing and mechanical strength, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 2,5-dimercapto-1,3 ,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol Erythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate), and trimethylolpropane-tris(3-mercaptopropio) nate) may be used at least one selected from the group consisting of.

The adhesion promoter used herein includes methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, and methacryloyloxy propyldimethoxysilane. It is possible to select and use at least one type of methacryloyl silane coupling agent such as, and at least one type of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc. as the alkyl trimethoxysilane. You can choose to use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 manufactured by BYK-Chemie. , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.

The antioxidant may be at least one selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-g, t-Butylphenol 4,4'-butylidene-bis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol) or bis[3 ,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester), such as a hindered phenol-based primary antioxidant; amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N′-diphenyl-p-phenylenediamine or N,N′-di-β-naphthyl-p-phenylenediamine secondary antioxidants; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane secondary antioxidants; or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4' -Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester) may be mentioned as a phosphite-based secondary antioxidant.

As the ultraviolet absorber, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but the present invention is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and may include one or more selected from the group consisting of phenothiazine (phenothiazine), but is not limited thereto. may include those generally known in the art.

The dispersant may be used as a method of internally adding the pigment to the pigment in the form of surface-treating the pigment in advance, or a method of externally adding the pigment to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and fluorine-based, ester-based, cationic, anionic, nonionic, and amphoteric surfactants may be mentioned. These may be used individually or in combination of 2 or more types.

Specifically, the dispersant is polyalkylene glycol and its esters, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylate esters, carboxylates, There is at least one selected from the group consisting of an alkylamide alkylene oxide adduct and an alkylamine, but is not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of the nonpolymeric leveling agent include non-polymeric sulfur-containing and non-polymeric nitrogen-containing The compounds include, but are not limited to, those commonly used in the art may be used.

According to an exemplary embodiment of the present specification, there is provided a photosensitive material manufactured using the photosensitive resin composition.

More specifically, the photosensitive resin composition of the present specification is applied on a substrate by an appropriate method to form a thin film or patterned photosensitive material.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, etc. may be used, and in general, a spin coating method is widely used. In addition, after forming the coating film, in some cases, the residual solvent may be partially removed under reduced pressure.

The light source for curing the photosensitive resin composition according to the present specification includes, for example, a mercury vapor arc emitting light having a wavelength of 250 nm to 450 nm, a carbon arc, an Xe arc, and the like, but is not necessarily limited thereto.

The photosensitive resin composition according to the present specification is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode , photosensitive material for overcoat layer formation, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There is no particular limitation.

According to an exemplary embodiment of the present specification, there is provided a color filter including the photosensitive material.

The color filter may be manufactured using a photosensitive resin composition including the compound represented by Formula 1 above. A color filter may be formed by coating the photosensitive resin composition on a substrate to form a coating film, and exposing, developing and curing the coating film.

The photosensitive resin composition according to an exemplary embodiment of the present specification has excellent heat resistance, and there is little change in color due to heat treatment. can

The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and the type is not particularly limited.

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

According to another exemplary embodiment, the color filter may further include an overcoat layer.

A grid-like black pattern called a black matrix may be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching may be used. However, in consideration of the high cost in the process, the high reflectivity of chromium, and environmental pollution caused by the chromium waste solution, a resin black matrix by a pigment dispersion method capable of fine processing may be used.

The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black alone or a mixture of carbon black and a colored pigment can be used. At this time, since a colored pigment lacking in light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material is relatively increased. There are advantages to not being.

A display device including a color filter according to the present specification is provided.

The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be any one of a liquid crystal display device (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

<Example>

[Preparation Example 1: Preparation of Compound A]

[A-1] (Benzenesulfonate Dichlorosulfofluorescein)(3g, 7.40mmol, 1eq), [A-2](2-(Ethylamino)ethanol)(5.28g, 59.22mmol, 8eq), DI in a 100mL 1-neck round-bottom flask -After adding 50 g of water, it was stirred at 100 °C. Then, the mixture was stirred for 20 hours. The reaction was terminated by quenching in 1M HCl solution, and sodium chloride (NaCl) was added to precipitate the reaction.

The resulting precipitate was filtered under reduced pressure and dried in an oven at 80°C. After drying, to remove NaCl between the products, it was dissolved in DMF (dimethylformamide) and filtered, and the filtrate was quenched with diethyl ether, filtered under reduced pressure, and dried to obtain compound [A] (2.98 g, 5.84 mmol, 78.9%). .

Ionization mode: APCI +:m/z = 510 [M+H]+, Exact Mass: 510.18

[Preparation Example 2: Preparation of Compound B]

[A-1] (Benzenesulfonate Dichlorosulfofluorescein)(3g, 7.40mmol, 1eq), [A-2] (2-(Ethylamino)ethanol)(1.0g, 11.2mmol, 1.51eq), After adding 50 g of DI-water, it was stirred at 100 °C. Then, the mixture was stirred for 20 hours. The reaction was terminated by quenching in 1M HCl solution, and sodium chloride (NaCl) was added to precipitate the reaction. The resulting precipitate was filtered under reduced pressure and dried in an oven at 80°C. After drying, in order to remove NaCl between the products, it was dissolved in DMF (dimethylformamide), filtered, and the filtrate was quenched with diethyl ether, filtered under reduced pressure, and dried. Thereafter, the precipitate was separated through column chromatography. (Eluent Dichloromethane:Metanol=10:1) As a result, compound [B] (1.3 g, 2.8 mmol) was obtained, and the yield was 37.8%.

Ionization mode: APCI +:m/z = 457 [M+H]+, Exact Mass: 457

[Preparation Example 3: Preparation of Compound C]

Compound [B] (1g, 2.19mmol, 1eq), Compound [A-3] Diethylamine (0.24g, 3.29mmol, 1.5eq) was added and prepared in the same manner as in Preparation Example 2 at room temperature, Compound [C] 0.8g ( 1.6 mmol) was obtained. (Yield: 73.0%)

Ionization mode: APCI +:m/z = 494 [M+H]+, Exact Mass: 494

[Preparation Example 4: Preparation of Compound 1]

Compound [A] (1.5 g, 2.94 mmol, 1eq) was dissolved in a mixture of 5 g of Dichloromethane in 25 g of Tetrahydrofuran. 4-nitrobenzoyl chloride (2.72g, 14.7mmol, 5eq) and triethylamine (0.9g, 8.82mmol, 3eq) were added and heated at 60°C. After about 24 hours of reaction, the reaction was terminated by quenching with 1M HCl solution, followed by filtration under reduced pressure. Purification by column chromatography (Dichloromethane:Metanol=8:1) gave compound [1] 1.6g (2.0mmol). (Yield 68%)

Ionization mode: APCI +:m/z = 808 [M+H]+, Exact Mass: 808

[Preparation Example 5: Preparation of Compound 2]

Compound [A] (1.5g, 2.94mmol, 1eq), 4-fluorobenzoyl chloride (2.32g, 14.7mmol, 5eq) and triethylamine (0.9g, 8.82mmol, 3eq) were added and prepared as in Preparation Example 4, and the compound [ 2] 1.6 g (2.12 mmol) was obtained. (yield 72%)

Ionization mode: APCI +:m/z = 754 [M+H]+, Exact Mass: 754

[Preparation Example 6: Preparation of Compound 3]

Compound [A] (1.5g, 2.94mmol, 1eq), 2-methoxybenzoyl chloride (2.50g, 14.7mmol, 5eq) and triethylamine (0.9g, 8.82mmol, 3eq) were added and prepared as in Preparation Example 4, and the compound [ 3] 1.6 g (2.10 mmol) was obtained. (yield 70%)

Ionization mode: APCI +:m/z = 778 [M+H]+, Exact Mass: 778

[Preparation Example 7: Preparation of Compound 4]

Compound [A] (1.5g, 2.94mmol, 1eq), 4-((trifluoromethyl)sulfonyl)benzoyl chloride (4.00g, 14.7mmol, 5eq) and Triethylamine (0.9g, 8.82mmol, 3eq) were put in Preparation Example 4 1.8 g (1.80 mmol) of compound [4] was obtained. (Yield 61.2%)

Ionization mode: APCI +:m/z = 982 [M+H]+, Exact Mass: 982

[Preparation Example 8: Preparation of compound 5]

Compound [A] (1.5g, 2.94mmol, 1eq), 2,6-dinitro-6-(trifluoromethyl)benzoyl chloride (4.38g, 14.7mmol, 5eq) and Triethylamine (0.9g, 8.82mmol, 3eq) were added and prepared It was prepared as in Example 4 to obtain 2.0 g (1.90 mmol) of compound [5]. (Yield 65%)

Ionization mode: APCI +:m/z = 1034 [M+H]+, Exact Mass: 1034

[Preparation Example 9: Preparation of Compound 6]

Compound [A] (1.5g, 2.94mmol, 1eq), 2-(thiophene-2-yl)acetyl chloride (2.35g, 14.7mmol, 5eq) and Triethylamine (0.9g, 8.82mmol, 3eq) were added and prepared above 4 was prepared to obtain 1.3 g (1.70 mmol) of compound [6]. (Yield 57.8%)

Ionization mode: APCI +:m/z = 758 [M+H]+, Exact Mass: 758

[Preparation Example 10: Preparation of compound 7]

Compound [A] (1.5g, 2.94mmol, 1eq), 3-(methylthio)propanoyl chloride (2.03g, 14.7mmol, 5eq) and Triethylamine (0.9g, 8.82mmol, 3eq) were added and prepared as in Preparation Example 4 1.0 g (1.40 mmol) of compound [7] was obtained. (Yield 47.6%)

Ionization mode: APCI +:m/z = 714 [M+H]+, Exact Mass: 714

[Preparation Example 11: Preparation of compound 8]

Compound [A] (1.5g, 2.94mmol, 1eq), 4-nitrobenzoyl chloride (0.8g, 4.41mmol, 1.5eq) and triethylamine (0.44g, 4.41mmol, 1.5eq) were added and prepared as in Preparation Example 4, and the compound [8] 0.8 g (1.21 mmol) was obtained. (Yield 41.1%)

Ionization mode: APCI +:m/z = 659 [M+H]+, Exact Mass: 659

[Preparation Example 12: Preparation of compound 9]

Compound [C] (1.5g, 3.03mmol, 1eq), 2-chloro-4-fluorobenzoyl chloride (1.74g, 9.09mmol, 3eq) and triethylamine (0.77g, 7.58mmol, 2.5eq) were added as in Preparation Example 4 was prepared to obtain 1.0 g (1.5 mmol) of Compound [9]. (Yield 49.5%)

Ionization mode: APCI +:m/z = 650 [M+H]+, Exact Mass: 650

[Preparation Example 13: Preparation of Compound 10]

Compound [9] 1.0g (1.5mmol, 1eq) and Phosphorus oxychloride 1.15g (7.5mmol, 5eq) were added and stirred at 60°C for about 2 hours. The obtained reaction solution was allowed to cool to room temperature, and the reaction solution was slowly added dropwise to 1.5 L of ice water, followed by stirring for about 30 minutes. The obtained crystals were separated by filtration, washed with 200 mL of distilled water and dried under reduced pressure to obtain 0.9 g (1.34 mmol) of compound 9-1. (yield 89.3%)

Dissolve 0.9 g (1.34 mmol, 1 eq) of compound [9-1] in 40 mL of Chloroform. Diethylamine 0.2g (2.68mmol, 2eq) was added dropwise and stirred at room temperature for about 2 hours. Thereafter, 100 mL of distilled water was added to the obtained reaction solution, washed with water, and then the organic layer was extracted with Chloroform and dried under reduced pressure. The obtained compound was purified by column chromatography (Dichloromethane:Methanol=8:1) to obtain 0.55 g (0.74 mmol) of compound [10]. (Yield 55.2%)

Ionization mode: APCI +:m/z = 706 [M+H]+, Exact Mass: 706

[Preparation Example 13: Preparation of compound 11]

Compound [10] 0.55g (0.74mmol, 1eq) was dissolved in 30 mL of methanol, 0.8g (2.85mmol, 3.85eq) of bis((trifluoromethyl)sulfonyl)amide was added, and the mixture was stirred at room temperature for about 2 hours. The reactant was added dropwise to 200 mL of distilled water and extracted with Chloroform to obtain 0.6 g (0.66 mmol) of [Compound 11]. (yield 89.2%)

Ionization mode: APCI +:m/z = 706 [M+H]+, Exact Mass: 706

Ionization mode: APCI-:m/Z = 280 [M-H], Exanct Mass: 279

[Comparative Example Compound]

As a comparative example compound, rhodamine B was used.

<Preparation of photosensitive resin composition Example 1>

Based on 100 parts by weight of the total weight of the photosensitive resin composition, 0.4 parts by weight of the compound [1], 78.18 parts by weight of binder A, 0.6 parts by weight of leveling agent F-554, 0.08 parts by weight of adhesive agent KBM-503, 20.74 parts by weight of solvent (DMF, Dimethylformamide) A photosensitive resin composition Example 1 was prepared by mixing parts by weight.

The binder A is a copolymer having a mass ratio of benzyl methacrylate; N-phenylmaleimide; styrene; methacrylic acid = 55:9:11:25.

<Preparation of photosensitive resin composition Examples 2 to 10>

Photosensitive resin composition Examples 2 to 10 were prepared in the same manner as in the photosensitive resin composition Example 1, except that the compound [1] of the photosensitive resin composition Example 1 was applied as the compounds shown in Table 1 below.

Example One 2 3 4 5 6 7 8 9 10 compound One 2 3 4 5 6 7 8 9 11

<Preparation of photosensitive resin composition Comparative Example 1>

A resin composition Comparative Example 1 was prepared in the same manner as in the photosensitive resin composition Example 1, except that the compound of the photosensitive resin composition Example 1 was changed to the compound of the comparative example (rhodamine B).

Experimental example

[Substrate production]

The photosensitive resin compositions prepared in Examples 1 to 10 and Comparative Example 1 were spin-coated on glass (5 cm X 5 cm) and subjected to prebake at 100° C. for 100 seconds to form a film. After the pre-heat treatment, the substrate was manufactured by post-bake at 230°C for 20 minutes.

[Heat resistance evaluation]

An absorption spectrum in a wavelength range of 380 to 780 nm was obtained by using a spectrometer (MCPD, Otsuka Co.) for the post-bake substrate prepared under the above conditions.

In addition, the transmittance spectrum was obtained in the same measurement range as the same equipment by additionally processing the post heat treatment substrate (post bake once) at 230° C. for 100 minutes.

ΔEab was calculated by Equation 1 below using the values L*, a*, and b* obtained from the absorption spectrum obtained using the C light source as a backlight, and is shown in Table 2 below.

[Formula 1]

ΔEab(L*, a*, b*) = {(ΔL*) ² +(Δa*) ² +(Δb*) ² } ^1/2

A small ΔEab value means less color change, indicating excellent heat resistance.

△Eab Comparative Example 1 62.44 Example 1 6.52 Example 2 4.58 Example 3 6.82 Example 4 5.30 Example 5 3.91 Example 6 4.91 Example 7 10.61 Example 8 5.72 Example 9 5.62 Example 10 3.52

According to Table 2, since the ΔEab value of Examples 1 to 10 is very small compared to Comparative Example 1, it is possible to obtain a photosensitive resin composition and color filter having excellent heat resistance by using the compound according to an exemplary embodiment of the present specification. was confirmed.

[Fluorescence intensity evaluation]

The fluorescence intensity was obtained using a fluorescence meter (FS-2, Sinco) for the post-heat treatment (post bake once) substrate prepared under the above conditions.

The fluorescence intensity of the compounds of Examples 1 to 10 was compared with 100% of the fluorescence intensity of the compound rhodamine B according to Comparative Example 1 and shown in Table 3 below.

Fluorescence intensity Comparative Example 1 100% Example 1 28.6% Example 2 58.3% Example 3 62.3% Example 4 50.5% Example 5 34.7% Example 6 57.5% Example 7 30.0% Example 8 26.8% Example 9 59.7% Example 10 43.8%

According to Table 3, it can be seen that the fluorescence intensity of Examples 1 to 10 is lower than that of Comparative Example 1. By using the compound according to an exemplary embodiment of the present specification, a photosensitive resin composition having reduced fluorescence intensity can be obtained. there was.

Claims (11)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L1 and L2 are the same as or different from each other, and each independently a direct bond; -L'-OCO-L''; or an unsubstituted alkylene group,
The L' and L'' are the same as or different from each other, and each independently a direct bond; Or an unsubstituted alkylene group,
A1 and A2 are the same as or different from each other, and are each independently an unsubstituted alkyl group,
B1 and B2 are the same as or different from each other, and each independently hydrogen; hydroxyl group; A hydroxy group, a thiophene group, or an alkyl group unsubstituted or substituted with _{-SCH 3 ;} or an aryl group substituted with a methyl group substituted with a nitro group, a nitrile group, fluorine, chlorine, a methoxy group, -SO ₂ CF ₃ , -CF _{3 or chlorine,}
R1 to R3 are the same as or different from each other, and each independently hydrogen; sulfonamide group; sulfonate group; or an anionic group,
r1 is an integer of 1 to 5, and when r1 is 2 or more, R1 of 2 or more are the same as or different from each other,
r2 and r3 are integers from 0 to 3, and when r2 and r3 are 2 or more, the structures in parentheses are the same as or different from each other,
X is an anionic group,
a is an integer of 0 or 1. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 2:
[Formula 2]

In Formula 2,
L1, A1, A2, B1, R1 to R3, r1 to r3, X and a are as defined in Formula 1 above,
L3 is an unsubstituted alkylene group,
B3 is a hydroxy group, a thiophene group, or an alkyl group unsubstituted or substituted with _{-SCH 3 ;} or an aryl group substituted with a methyl group substituted with a nitro group, a nitrile group, a fluorine, chlorine, a methoxy group, -SO ₂ CF ₃ , -CF _{3 or chlorine.} The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 3:
[Formula 3]

In Formula 3,
A1, A2, R1 to R3, r1 to r3, X and a are as defined in Formula 1 above,
L3 and L4 are the same as or different from each other, and are each independently an unsubstituted alkylene group,
B3 and B4 are the same as or different from each other, and each independently a hydroxyl group, a thiophene group, or an alkyl group unsubstituted or substituted with _{-SCH 3 ;} or an aryl group substituted with a methyl group substituted with a nitro group, a nitrile group, a fluorine, chlorine, a methoxy group, -SO ₂ CF ₃ , -CF _{3 or chlorine.} The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following Formulas:

In the above formula, X is as defined in claim 1. A color material composition comprising the compound of any one of claims 1 to 4, and further comprising at least one of a dye and a pigment. The method according to claim 5, wherein the dye is selected from xanthene-based dyes, cyanine-based dyes, anthraquinone-based dyes, porphyrin-based dyes, triarylmethane-based dyes, azo metal complexes, coumarin-based dyes, azo-based dyes and quinophthalone-based dyes. One or more dyes that become
The pigment is a blue pigment, a purple pigment or a yellow pigment. The compound of any one of claims 1 to 4; binder resin; polyfunctional monomers; photoinitiators; And a photosensitive resin composition comprising a solvent. The method according to claim 7, The content of the compound represented by Formula 1 based on the total weight of the solid content in the resin composition is 5% to 60% by weight,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1 wt% to 20 wt%,
The content of the polyfunctional monomer is 0.1% to 50% by weight of the photosensitive resin composition. A photosensitive material manufactured using the photosensitive resin composition according to claim 7. A color filter comprising the photosensitive material according to claim 9 . A display device comprising the color filter according to claim 10 .