JP2017210615A - Compounds, color material compositions containing the same, and resin compositions containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide novel color materials capable of improving the color reproduction, the luminance and the contrast ratio.SOLUTION: The novel compounds are represented by, e.g., the compound prepared by the reaction of the formula in the figure. Also provided are color material compositions containing the compounds, and resin compositions containing the compounds.SELECTED DRAWING: None

Description

  The present specification relates to a compound, a colorant composition containing the compound, and a resin composition containing the compound.

  Recently, a color filter is required to have a performance characterized by high brightness and high contrast ratio. One of the main purposes of display element development is to differentiate display element performance by improving color purity and to improve productivity in the manufacturing process.

  Conventionally, a pigment type used as a color material for a color filter is present in a color photoresist in a particle-dispersed state, so that it has been difficult to adjust brightness and light / dark ratio by adjusting the size and distribution of pigment particles. In the case of pigment particles, dissolution and dispersibility are reduced by aggregation in the color filter, and multiple scattering of light is caused by large particles that are aggregated. Such scattering of polarized light has been pointed out as a main cause of lowering the contrast ratio. Efforts to improve the brightness and light-to-dark ratio by making the pigments ultra fine and dispersion stable continue, but the degree of freedom is limited in the selection of color materials to achieve color coordinates for high color purity display devices . In addition, the pigment dispersion method using a color material that has already been developed, particularly a pigment, has a limit in improving the color purity, luminance, and contrast ratio of a color filter using the color material.

  Accordingly, there is a demand for development of a new color material that can improve color reproduction, luminance, and contrast ratio by increasing color purity.

Korean Published Patent No. 2012-0139606

  The present specification provides a compound, a colorant composition containing the compound, and a resin composition containing the compound.

One embodiment of the present specification provides a compound represented by Formula 1 below.
[Chemical Formula 1]
In Formula 1,
Y1 and Y2 are each independently a direct bond; or CQ1Q2,
Two or more adjacent groups of Q1, Q2, and R6 to R13 are bonded to each other to form at least one or more substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms. A ring; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms,
Q1, Q2, R1 to R5 and R6 to R13, which do not form a ring with adjacent groups, are each independently hydrogen, deuterium, halogen group, nitro group, hydroxy group, substituted or unsubstituted carbon number A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted carbon number 2 Selected from the group consisting of ˜30 monocyclic or polycyclic heteroaryl groups.

  Another embodiment of the present specification provides a colorant composition including the compound represented by Formula 1.

  Another embodiment of the present specification provides a resin composition including the colorant composition.

  Since the compound according to an embodiment of the present specification can act as a dye, it can be used as a color filter material.

  The resin composition containing the compound according to an embodiment of the present specification is excellent in color characteristics, heat resistance, and solvent resistance.

  In addition, the resin composition containing the compound according to an embodiment of the present specification plays a role of preventing reagglomeration of the atomized pigment and generation of foreign matters, and when applied to a color filter, the light / dark ratio is improved. To do.

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

  One embodiment of the present specification provides a compound represented by Formula 1. Formula 1 is characterized in that at least one of the substituents R6 to R13 is a nitro group. The nitro group can play a role of electron withdrawing in the whole compound.

  In the present specification, examples of the substituent are described below, but are not limited thereto.

  The term “substituted” means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is a position where a hydrogen atom is substituted, that is, the substituent is substituted. There is no limitation as long as it is possible, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

  In this specification, the term “substituted or unsubstituted” refers to deuterium, halogen group, alkyl group, alkenyl group, alkoxy group, cycloalkyl group, silyl group, aralkyl group, aralkenyl group, ester group, carbonyl group, Aryloxy group; alkylthioxy group; alkylsulfoxy group; arylsulfoxy group; boron group; alkylamine group; aralkylamine group; arylamine group; heteroaryl group; carbazole group; Substituted with one or more substituents selected from the group consisting of: a group; a nitrile group; a nitro group; a hydroxy group; a cyano group, and a heterocyclic group containing one or more of N, O, S, or P atoms Or a substituent to which two or more of the exemplified substituents are linked. Or substituted, or means that does not have any substituent. For example, the “substituent in which two or more substituents are linked” may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are linked.

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

  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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl. , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- Propyl, 1,1-dimethyl-propyl, iso Hexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl there are such as, but not limited to.

  In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3- Butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1- Yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

  In the present specification, the alkoxy group may be a straight chain, a branched chain, or a ring chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n- Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like are limited thereto. It is not something.

  In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 20 carbon atoms, and in particular, may be a cyclopentyl group or a cyclohexyl group.

  In the present specification, specifically, in the aralkyl group, the aryl moiety is applicable to the description of aryl described later, but has 6 to 49 carbon atoms, and the alkyl moiety has 1 to 44 carbon atoms. . Specific examples include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, α-methylbenzyl group, α, α- Dimethylbenzyl group, α, α-methylphenylbenzyl group, 1-naphthylbenzyl group, 2-naphthylbenzyl group, p-fluorobenzyl group, 3,5-difluorobenzyl group, α, α-ditrifluoromethylbenzyl group, p -Methoxybenzyl group, m-methoxybenzyl group, α-phenoxybenzyl group, α-benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, pyrrolylethyl group, aminobenzyl group, nitrobenzyl group, Cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1- And the like Lolo 2-phenyl isopropyl group, but not limited thereto.

  In the present specification, the aryl part of the aralkenyl group can be described with respect to aryl described later, and the alkenyl part can be applied with the description of alkenyl group described above.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

  In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

  When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrycenyl group, fluorenyl group, or the like, but is not limited thereto.

  In the present specification, the fluorenyl group may be substituted, or adjacent substituents may be bonded to each other to form a ring.

When the fluorenyl group is substituted,
However, it is not limited to these.

  In the present specification, a heteroaryl group includes one or more atoms that are not carbon and hetero atoms, and specifically, the hetero atoms are selected from the group consisting of O, N, Se, and S. One or more atoms may be included. Although carbon number of a heteroaryl group is not specifically limited, It is preferable that it is C2-C60. Examples of heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, triazole group, acridyl Group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolyl group, indole group, carbazole group, benzoxazole group, benzimidazole Group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, Kisajiazoriru group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and the like dibenzofuranyl group, but is not limited to only these.

  In the present specification, the description of the aryl group is applicable except that the aromatic hydrocarbon ring is not a monovalent substituent.

  In this specification, the description of a heteroaryl group is applicable except that the heterocycle is not a monovalent substituent.

  As used herein, an “adjacent” group refers to a substituent substituted by an atom directly linked to the atom to which the substituent is substituted, a substituent that is sterically closest to the substituent, or the It can mean other substituents in which the substituent is replaced by a substituted atom. For example, two substituents substituted in the ortho position on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring are interpreted as “adjacent” groups to each other.

  In the present specification, the meaning that adjacent groups are bonded to each other to form a ring means that, as described above, adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring, or 5 to 8 members. This means forming a member heterocycle, which may be monocyclic or polycyclic, aliphatic, aromatic, or a condensed form thereof, and is not limited thereto.

  According to one embodiment of the present specification, R 1 to R 13 each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; An unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic group having 2 to 30 carbon atoms Selected from the group consisting of heteroaryl groups, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least 1 One or more substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon rings having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic hetero rings having 2 to 30 carbon atoms; To form.

  According to one embodiment of the present specification, R 1 to R 13 each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; An unsubstituted alkoxy group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic group having 2 to 20 carbon atoms Selected from the group consisting of heteroaryl groups, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least 1 One or more substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon rings having 6 to 20 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic hetero rings having 2 to 20 carbon atoms; To form.

  According to one embodiment of the present specification, R1 to R13 each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted monocyclic or polycyclic having 6 to 15 carbon atoms. Selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, at least one of R6 to R13 is a nitro group, and R6 At least two or more adjacent groups of ˜R13 are bonded to each other to form at least one or more substituted or unsubstituted mono- or polycyclic aromatic hydrocarbon rings having 6 to 15 carbon atoms; or substituted Alternatively, an unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 15 carbon atoms is formed.

  According to one embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen; deuterium; halogen group; nitro group; and hydroxy group, and at least one of R6 to R13. The above is a nitro group, and at least two of R6 to R13 adjacent to each other are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic group having 6 to 10 carbon atoms. A hydrocarbon ring; or a substituted or unsubstituted monocyclic heterocycle having 2 to 10 carbon atoms.

  According to one embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen; deuterium; halogen group; nitro group; and hydroxy group, and at least one of R6 to R13. The above is a nitro group, and at least two of R6 to R13 adjacent to each other are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic group having 6 to 10 carbon atoms. A hydrocarbon ring is formed.

According to one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.
[Chemical formula 2]
[Chemical formula 3]
In Formulas 2 and 3,
Y1, Y2, R1 to R13 are as defined in Chemical Formula 1,
R14, R15 and R6 ′ to R15 ′ each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon number An alkoxy group having 1 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Selected from the group consisting of
One or more of R6 ′ to R9 ′ in Chemical Formula 2 and one or more of R10 ′ to R13 ′ in Chemical Formula 3 are nitro groups.

  In Formulas 2 and 3, R1 to R13 each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon. An alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms And at least two or more adjacent groups selected from the group consisting of R6 to R13 are bonded to each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms. Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, wherein R14, R15 and R6 ′ to R15 ′ are each Hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; and substituted or unsubstituted Selected from the group consisting of a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and R6 ′ to R13 ′ At least one of them is a nitro group.

  According to one embodiment of the present specification, R 1 to R 13 each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; An unsubstituted alkoxy group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic group having 2 to 20 carbon atoms Selected from the group consisting of heteroaryl groups, and at least two or more adjacent groups of R 6 to R 13 are bonded to each other to form at least one or more substituted or unsubstituted monocyclic groups having 6 to 20 carbon atoms or A polycyclic aromatic hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 20 carbon atoms.

  According to one embodiment of the present specification, R1 to R13 each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted monocyclic or polycyclic having 6 to 15 carbon atoms. Selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, and at least two of R6 to R13 are adjacent to each other. At least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 15 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 15 carbon atoms; Form a ring.

  According to one embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen; deuterium; halogen group; nitro group; and hydroxy group; and at least two of R6 to R13 The groups adjacent to each other are bonded to each other and have at least one or more substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon rings having 6 to 15 carbon atoms; or substituted or unsubstituted carbon atoms having 2 to 2 carbon atoms. 15 monocyclic or polycyclic heterocycles are formed.

  According to one embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen; deuterium; halogen group; nitro group; and hydroxy group; and at least two of R6 to R13 The groups adjacent to each other are bonded to each other to form at least one or more substituted or unsubstituted monocyclic aromatic hydrocarbon rings having 6 to 10 carbon atoms; or substituted or unsubstituted single atoms having 2 to 10 carbon atoms. To form a heterocycle of the ring.

  According to one embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen; deuterium; halogen group; nitro group; and hydroxy group; and at least two of R6 to R13 The groups adjacent to each other are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms.

  According to one embodiment of the present specification, R 14, R 15 and R 6 ′ to R 15 ′ are each independently hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted C 1-10. A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms; and a substituted or unsubstituted carbon group having 2 to 15 carbon atoms; And at least one of R6 ′ to R13 ′ is a nitro group.

  According to one embodiment of the present specification, R14, R15, and R6 ′ to R15 ′ each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; and substituted or unsubstituted carbon atoms having 6 to 6 carbon atoms. Selected from the group consisting of 10 monocyclic aryl groups; and substituted or unsubstituted monocyclic heteroaryl groups having 2 to 10 carbon atoms, wherein at least one of R6 ′ to R13 ′ is a nitro group is there.

  According to one embodiment of the present specification, R 14, R 15 and R 6 ′ to R 15 ′ are each independently selected from the group consisting of hydrogen; deuterium; halogen group; and nitro group, and R 6 ′ to R 13 ′ At least one of them is a nitro group.

According to one embodiment of the present specification, the chemical formula 1 may provide a compound represented by the following chemical formula 4.
[Chemical formula 4]
In Formula 4,
R1 to R5, R14, R15 and R6 ′ to R15 ′ are the same as described above.

  According to one embodiment of the present specification, the chemical formula 1 provides a compound in which at least one of R6 to R9 is a halogen element.

  According to one embodiment of the present specification, in the Chemical Formulas 2 and 3, at least one of R9 ′ and R13 ′ is a nitro group.

According to one embodiment of the present specification, the compound represented by Formula 1 provides a compound represented by any one of the following compounds.

  Another embodiment of the present specification provides a colorant composition comprising a compound according to one embodiment of the present specification.

  The color material composition may further include at least one of a dye and a pigment in addition to the compound of Chemical Formula 1. For example, the colorant composition may include only the compound according to one embodiment of the present specification, but may include the compound of Formula 1 and one or more dyes, or may be related to one embodiment of the present specification. A compound and one or more pigments may be included, or the compound of Formula 1 may be included, one or more dyes, and one or more pigments.

  In one embodiment of the present specification, a resin composition including the color material composition is provided.

  In one embodiment of the present specification, the resin composition may further include a binder resin; a multifunctional monomer; a photoinitiator; 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 produced from the resin composition.

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

  The polyfunctional monomer imparting the mechanical strength of the film may be any one or more of unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. There may be.

  Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl (meth) acrylate. , T-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2- Droxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytri Propylene 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-hexafluo Isopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl It may be selected from the group consisting of acrylate and butyl α-hydroxymethyl acrylate, but is not limited thereto.

  Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p ) -Chlorostyrene may be selected from the group consisting of, but not limited to.

  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 may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. However, it is not limited to these.

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

  The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group. For example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2- Selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxypolycaprolactone mono (meth) acrylate Although it is preferable to use 1 or more types, it is not limited only to these.

  In one 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 plays a role of forming a photoresist image by light. Specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6 -Hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, penta Erythritol tetramethacrylate and dipentaerythritol Be one or a mixture of two or more selected from the group consisting of hexamethylene methacrylate may.

  The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light and causes crosslinking. For example, from the group consisting of an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more selected.

  The acetophenone compounds include 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-hydroxycyclohexyl phenylketone, benzoin methyl ether, benzoin ethyl 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-morpholino-1-one include, but are not limited to.

  Examples of the biimidazole compound include 2,2-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 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' Examples include, but are not limited to, tetraphenylbiimidazole, 2,2′-bis (o-chlorophenyl) -4,4,5,5′-tetraphenyl-1,2′-biimidazole.

  The triazine 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-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-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-triazin-6-yl] phenylthio} propionic acid, 3- {4 -[2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloromethyl) -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 Yes, it is not limited to these.

  The oxime compounds are 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigy, CGI124), ethanone, -1- (9-ethyl) -6. Examples include-(2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGI242), N-1919 (Adeka), and the like, but are 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-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3- It may be one or more selected from the group consisting of ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is limited to this. It is not a thing.

  In one embodiment of the present specification, the content of the compound of Formula 1 is 5% by weight to 60% by weight based on the total weight of the solid content in the resin composition, and the content of the binder resin Is from 1 wt% to 60 wt%, the photoinitiator content is from 0.1 wt% to 20 wt%, and the polyfunctional monomer content is from 0.1 wt% to 50 wt%. % By weight.

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

  In one embodiment of the present specification, the resin composition includes a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, an antioxidant, a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant, It additionally contains one or more additives selected from the group consisting of a dispersant and a leveling agent.

  In one embodiment of the present specification, the content of the additive is 0.1 wt% to 20 wt% based on the total weight of the solid content in the resin composition.

  The photocrosslinking sensitizer includes benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3, Benzophenone compounds such as 3-dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 A fluorenone compound such as fluorenone; a thioxanthone compound such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; Xanthone compounds such as nthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine Acridine compounds such as 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; Dicarbonyl compounds such as 7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione and 9,10-phenanthrenequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6- Dimethoxybenzoyl) -2,4,4-trimethylpentyl Phosphine oxide compounds such as sphin oxide; benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2 , 5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl-cyclopentanone, etc. 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7 -Methoxy-coumarin, 10,10-ca Such as rubonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolizin-11-one One or more selected from the group consisting of coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthothiazoline can be used. .

  The curing accelerator is used to increase curing and mechanical strength. Specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2 -Mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) It is possible to use one or more selected.

  As the adhesion promoter used in the present specification, a methacryloylsilane coupling agent such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane, etc. One or more of these can be selected and used, and as the alkyltrimethoxysilane, one or more selected from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, and the like can be used. .

  The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK manufactured by BYK-Chemie. -301, BYK-302, BYK-306, BYK-307, 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 and the like, and as the fluorine-based surfactant, IC (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. can be used. However, it is not limited to these.

  The antioxidant is at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant. However, it is not limited to this.

  Specific examples of antioxidants include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy -3,5-di-tert-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2, 4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 3,5-di-tert-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4- Methyl-6-tert-butylphenol), 2,6-g, tert-butylphenol 4,4′-butylidene-bis (3-methyl-6-tert-butylphenol) ), 4,4′-thiobis (3-methyl-6-tert-butylphenol), or bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester ( Hindered phenol-based primary antioxidants such as Bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl- Amine-based secondary antioxidants such as β-naphthylamine, N, N′-diphenyl-p-phenylenediamine, or N, N′-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilaurylthio Propionate, distearyl thiopropionate, merca Thio secondary antioxidants such as tobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phos Phyto, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Pentaerythritol Diphosphite), or (1,1′-biphenyl) -4,4′-diylbisphosphonic acid tetrakis [2 , 4-Bis (1,1-dimethylethyl) phenyl] ester ((1,1′-Biphenyl) -4,4′-Diylbisphosphonoacid acid tetrakis [2,4-bi (1,1-dimethylethyl) phenyl] phosphite secondary antioxidant such as ester) and the like.

  As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but are not limited thereto. Anything commonly used in the industry can be used.

  Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine 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 phenothiazine, but is not limited thereto and is generally known in the art. It can include those are.

  The dispersant can be used by a method of internally adding the pigment to the pigment in a form in which the pigment is surface-treated in advance or a method of adding the pigment to the pigment externally. As the dispersant, a compound type, nonionic, anionic, or cationic dispersant can be used, and a fluorine-based, ester-based, cationic-based, anionic-based, non-ionic, or amphoteric interface. An active agent etc. are mentioned.

  These can be used either individually or in combination of two or more.

  Specifically, the dispersant includes polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, and carboxylic acid. There is, but is not limited to, one or more selected from the group consisting of a salt, an alkylamide alkylene oxide adduct, and an alkylamine.

  The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamidoamine, reaction products of amines and epoxides, and non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric leveling agents. -Including but not limited to polymeric nitrogen-containing compounds, all commonly used in the art can be used.

  In one embodiment of the present specification, a photosensitive material manufactured with the resin composition is provided.

  In more detail, the resin composition of this specification is apply | coated on a base material by a suitable method, and the photosensitive material of a thin film or a pattern form is formed.

  Although it does not restrict | limit especially as said application | coating method, Spray method, roll coating method, spin coating method, etc. can be used, and spin coating method is generally used widely. Moreover, after forming a coating film, a part of residual solvent can be removed under reduced pressure depending on the case.

  Examples of the light source for curing the resin composition according to the present specification include, but are not necessarily limited to, a mercury vapor arc (arc), a carbon arc, and a Xe arc that emit light having a wavelength of 250 nm to 450 nm. Absent.

  The resin composition according to the present specification includes a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode. Used for coating layer forming photosensitive materials, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, photosensitive materials for printed wiring boards, plasma display panel (PDP) photosensitive materials, etc. And there is no particular limitation on its use.

  In one embodiment of the present specification, a color filter including the photosensitive material is provided.

  The color filter can be manufactured using a resin composition containing the compound represented by Formula 1. A color filter can be formed by applying the resin composition onto a substrate to form a coating film, and exposing, developing and curing the coating film.

  The resin composition according to one embodiment of the present specification is excellent in heat resistance, has little color change due to heat treatment, has a high color reproducibility even in the curing process during the production of a color filter, and has a luminance and light / dark ratio. A high color filter can be provided.

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

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

  In another embodiment, the color filter may further include an overcoat layer.

  A grid-like black pattern called a black matrix can be arranged between the color pixels of the color filter for the purpose of improving contrast. Chrome can be used as the black matrix material. In this case, it is possible to use a method in which chromium is deposited on the entire glass substrate and a pattern is formed by an etching process. However, a resin black matrix by a pigment dispersion method capable of fine processing can be used in consideration of high process cost, high reflectivity of chromium, and environmental contamination due to chromium waste liquid.

  In the black matrix according to an embodiment of the present specification, a black pigment or a black dye can be used as a coloring material. For example, carbon black can be used alone, or carbon black and colored pigment can be mixed and used. At this time, the amount of coloring material is relatively increased because of mixing colored pigments that lack light-shielding properties. However, there is an advantage that the strength of the film or the adhesion to the substrate does not decrease.

  A display apparatus 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 liquid crystal display (LCD). 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, the present specification will be described in detail with reference to examples. The following examples are intended to illustrate the present specification, and the scope of the present specification includes the ranges described in the following claims and their substitutions and modifications, and is not limited to the scope of the examples.

Synthesis example 1
Reaction formula 1
10 g (50.458 mmol) of 2,3-naphthalenedical carboxylic anhydride (A-1) was placed in 30 ml of HNO3, and the reaction solution was gradually warmed and stirred at 95 ° C. for 2 hours. The reaction solution was cooled to room temperature and precipitated in water. The precipitate was filtered under reduced pressure and dried in a 80 ° C. convection oven for 1 day to obtain A-2. The A-2 was put into 50 ml of Acetic anhydride, heated to 150 ° C. and stirred for 2 hours. The reaction product was cooled to room temperature, filtered under reduced pressure, and washed with a small amount of water to obtain 8.3 g (34.132 mmol) of A-3. The yield was 67.64%.

Synthesis example 2
Reaction formula 2
8-Aminoquinaldine (A-4) 3 g (18.963 mmol) and Phthalic anhydride (A-5) 2.809 g (18.963 mmol) were placed in 3 g of Benzoic acid and 3 g of methyl benzoate and gradually heated to 180 ° C. Stir for hours. The reaction was cooled to ambient temperature and precipitated into 100 ml MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried in a 80 ° C. convection oven for 1 day to obtain 4.67 g (16.198 mmol) of A-6, and the yield was 85.4%.

Synthesis example 3
Reaction formula 3
1.63 g (6.937 mmol) of A-3 and 2 g (6.937 mmol) of A-6 were placed in 3 g of Benzoic acid and 3 g of methyl benzoate, and the temperature was gradually raised and stirred at 200 ° C. for 3 hours. The reaction was cooled to ambient temperature and precipitated into 100 ml MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. The resultant was dried in a 80 ° C. convection oven for 1 day to obtain 12.422 g (4.717 mmol) of the resultant product according to the reaction scheme 3, and the yield was 68.0%.

Synthesis example 4
Reaction formula 4
Under the same conditions as those in Reaction Formula 2 and Reaction Formula 3, the resultant product according to Reaction Formula 4 was synthesized.

Synthesis example 5
Reaction formula 5
Under the same conditions as those in Reaction Formula 2 and Reaction Formula 3, the resulting product according to Reaction Formula 5 was synthesized.

Synthesis Example 6
Reaction formula 6
Under the same conditions as those in Reaction Formula 2 and Reaction Formula 3, the resulting product according to Reaction Formula 6 was synthesized.

Synthesis example 7
Reaction formula 7
Under the same conditions as those in the reaction formulas 2 and 3, the resultant product according to the reaction formula 7 was synthesized.

Synthesis example 8
Reaction formula 8
Under the same conditions as those in Reaction Formula 2 and Reaction Formula 3, the resultant product according to Reaction Formula 8 was synthesized.

  In Chemical Formula 3 of the present application, a specific example in which any one of R10 ′ to R15 ′ is a nitro group was synthesized by the same order and method as the results of Synthesis Examples 3-8.

Synthesis Example 9
Reaction formula 9
5 g (20.562 mmol) of A-3 and 3.253 g (20.562 mmol) of 8-Aminoquinaldine (A-4) were added to 5 g of Benzoic acid and 10 g of methyl benzoate, and the temperature was gradually raised and stirred at 180 ° C. for 5 hours. It was. The reaction was cooled to ambient temperature and precipitated into 150 ml MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried in a 80 ° C. convection oven for 1 day to obtain 7.094 g (18.505 mmol) of A-17, and the yield was 90.0%.

Synthesis Example 10
Reaction formula 10
5-17 g (13.043 mmol) of A-17 and 1.932 g (13.043 mmol) of Phthalic anhydride (A-5) were put into 5 g of Benzoic acid and 10 g of methyl benzoate, and the temperature was gradually raised and stirred at 200 ° C. for 3 hours. . The reaction was cooled to ambient temperature and precipitated into 150 ml MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried in a 80 ° C. convection oven for 1 day to obtain 5.022 g (9.781 mmol) of the resultant product according to the above reaction formula 10, and the yield was 74.97%.

Synthesis Example 11
Reaction formula 11
Under the same conditions as those of Reaction Formula 9 and Reaction Formula 10, the resulting product of Reaction Formula 11 was synthesized.

Synthesis Example 12
Reaction formula 12
Under the same conditions as those in Reaction Formula 9 and Reaction Formula 10, the resulting product according to Reaction Formula 12 was synthesized.

Synthesis Example 13
Reaction formula 13
Under the same conditions as those in Reaction Formula 9 and Reaction Formula 10, the resulting product according to Reaction Formula 13 was synthesized.

  In Chemical Formula 2 of the present application, a specific example in which any one of R6 ′ to R9 ′, R14, and R15 is a nitro group was synthesized by the same order and method as the results of Synthesis Examples 10-13.

Example 1
5.554 g of the resultant product according to Synthesis Example 3, copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value is 113 KOH mg / g, weight average molecular weight 20,000 measured by GPC, molecular weight Distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (BASF) 2.018 g, photopolymerizable compound DPHA ( Nippon Kayaku) 12.443g, Solvent PGMEA (Propylene Glycol Methylethyl Acetate) 68.593g, and DIC F-475, 1.016g as an additive were mixed to produce a compound.

Example 2
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 4 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 3
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 5 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 4
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 6 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 5
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 7 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 6
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 8 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 7
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 10 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 8
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 11 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 9
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 12 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Example 10
A compound was prepared in the same manner as in Example 1 except that 5.554 g of the resultant product of Synthesis Example 13 was used instead of the resultant product of Synthesis Example 3 of Example 1.

Comparative Example 1
A compound was produced in the same manner as in Example 1 except that the compound represented by the following chemical formula 5 was used in place of the resultant product obtained in Synthesis Example 3 of Example 1.
Chemical formula 5

Comparative Example 2
A compound was prepared in the same manner as in Example 1 except that the compound represented by the following chemical formula 6 was used instead of the resultant product obtained in Synthesis Example 3 of Example 1.
Chemical formula 6

Substrate preparation The compounds prepared in Examples 1 and 2 and Comparative Example 1 were spin-coated on glass (5 × 5 cm) and pre-baked at 100 ° C. for 100 seconds to form a film. It was. The distance between the substrate on which the film was formed and the photomask was 250 μm, and the entire surface of the substrate was irradiated with light having an exposure amount of 40 mJ / cm ² using an exposure machine.

  Thereafter, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post-baked at 230 ° C. for 20 minutes to produce a substrate.

Evaluation of heat resistance Using a spectroscope (MCPD-Otsuka Co., Ltd.), a transmittance spectrum in a visible light region in the range of 380 nm to 780 nm was obtained from a prebake substrate prepared under the above conditions. In addition, a pre-heat treatment substrate was additionally subjected to a post-heat treatment (post bake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum in the same equipment and measurement range.

Using the obtained transmittance spectrum and C light source backlight, ΔEab was calculated using the obtained value E (L *, a *, b *), and the results are shown in Table 1 below.
ΔE (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2

  A small ΔE value means excellent color heat resistance.

  Generally, when it has a value of ΔEab <3, it can be said that the colorant has excellent heat resistance.

  The heat resistance measurement results for the compound according to one embodiment of the present application and Comparative Example 1 are shown in Table 1 below. Further, as shown in Table 1, the compound according to one embodiment of the present application showed a color change (ΔEab) of 3 or less, similar to Comparative Example 1 (current commercial product). .

Evaluation of Long Wavelength After 0.05 g of the compound sample according to Examples 1, 4 and 7 and Comparative Example 2 was accurately weighed and put into a 200 ml volumetric flash, DMF was filled up to a 200 ml display line. Pipet 5 ml of this solution into a 100 ml volumetric flash and fill to the 100 ml mark with DMF. Using this solution, a UV-Vis absorption spectrum was measured using a UV-Vis Spectrophotometer, and the results are shown in Table 2 below.

  As is apparent from Table 2, it can be seen that the compound according to one embodiment of the present application has a longer wavelength than Comparative Example 2 in which the nitro group is not substituted. Accordingly, the compound according to an embodiment of the present application can have an advantage that the amount of the color material used is reduced by increasing the wavelength of the absorption spectrum.

Claims (14)

Compound represented by the following chemical formula 1:
[Chemical Formula 1]
In Formula 1,
Y1 and Y2 are each independently a direct bond; or CQ1Q2,
Two or more adjacent groups of Q1, Q2, and R6 to R13 are bonded to each other to form at least one or more substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms. A ring; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms,
Q1, Q2, R1 to R5 and R6 to R13, which do not form a ring with adjacent groups, are each independently hydrogen, deuterium, halogen group, nitro group, hydroxy group, substituted or unsubstituted carbon number A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted carbon number 2 Selected from the group consisting of ˜30 monocyclic or polycyclic heteroaryl groups. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2 or 3:
[Chemical formula 2]
[Chemical formula 3]
In Formulas 2 and 3,
Y1, Y2, R1 to R13 are as defined in Chemical Formula 1,
R14, R15 and R6 ′ to R15 ′ each independently represent hydrogen; deuterium; halogen group; nitro group; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon number An alkoxy group having 1 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Selected from the group consisting of
One or more of R6 ′ to R9 ′ in Chemical Formula 2 and one or more of R10 ′ to R13 ′ in Chemical Formula 3 are nitro groups. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4:
[Chemical formula 4]
In Formula 4,
R1 to R5, R14, R15 and R6 ′ to R15 ′ are the same as defined in claim 2.   The compound according to claim 1, wherein one or more of R 6 to R 13 is a nitro group.   The compound according to claim 1, wherein one or more of R6 to R9 is a halogen element.   The compound according to claim 2, wherein one or more of R9 'and R13' is a nitro group. 2. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following compounds:
.   The coloring material composition containing the compound of any one of Claims 1-7.   The colorant composition according to claim 8, further comprising at least one of a dye and a pigment.   The resin composition which further contains the compound of any one of Claims 1-7; binder resin; polyfunctional monomer; photoinitiator; and a solvent. Based on the total weight of solids in the resin composition, the content of the compound is 5 wt% to 60 wt%,
The content of the binder resin is 1 wt% to 60 wt%,
The content of the polyfunctional monomer is 0.1 wt% to 50 wt%,
The resin composition according to claim 10, wherein the content of the photoinitiator is 0.1 wt% to 20 wt%.   A photosensitive material produced using the resin composition according to claim 10.   A color filter comprising the photosensitive material according to claim 12.   A display device comprising the color filter according to claim 13.