KR20200069067A - Colorant composition, photosensitive resin composition, photo resist, color filter, and display device - Google Patents

Abstract

The present invention relates to a color material composition comprising a compound represented by chemical formula 1, to a photosensitive resin composition comprising the same, to a photosensitive material, to a color filter, and to a display device. The color material composition has excellent transmittance and pattern formation.

Description

Colorant composition, photosensitive resin composition, photosensitive material, color filter, and display device {COLORANT COMPOSITION, PHOTOSENSITIVE RESIN COMPOSITION, PHOTO RESIST, COLOR FILTER, AND DISPLAY DEVICE}

This specification relates to a color material composition and a photosensitive resin composition. In addition, the present specification relates to a photosensitive material, a color filter, and a display device manufactured using the photosensitive resin composition.

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

Since the pigment type used as a color material of a color filter existed in a color photoresist in a particle dispersion state, it was difficult to control the brightness and contrast ratios according to the pigment particle size and distribution control. In the case of pigment particles, aggregation and dispersibility are poor in a color filter, and multiple scattering of light occurs due to large particles aggregated. Scattering of the polarized light has been pointed out as a main factor that lowers the contrast ratio. Efforts are being made to improve the luminance and contrast ratio through ultra-fine atomization and dispersion stabilization of the pigment, but the degree of freedom is limited in selecting a color material for realizing color coordinates for a high-purity display device. In addition, the pigment dispersion method using color materials, especially pigments, which has already been developed, has reached a limit in improving the color purity, brightness, and contrast ratio of color filters using the same.

Accordingly, there is a need to develop a new color material capable of improving color purity, improving color reproduction, brightness and contrast ratio.

Korean Patent Publication No. 2001-0009058

The present inventors intend to provide a colorant composition and a photosensitive resin composition, a photosensitive material prepared using the same, a color filter, and a display device.

An exemplary embodiment of the present specification provides a color material composition comprising a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or N(R1)(R2), or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

m1 is an integer from 0 to 6, and when 2 or more, L1-A1 are the same or different from each other,

m2 is an integer from 0 to 6, and when 2 or more, L2-A2 is the same or different from each other,

m3 is an integer from 0 to 10, and when 2 or more, A3 is the same or different from each other,

n1 and n2 are the same as or different from each other, and each independently an integer of 0 or 1.

An exemplary embodiment of the present specification, a color material composition comprising a compound represented by the formula (1); Binder resin; Polyfunctional monomers; And it provides a photosensitive resin composition comprising a photoinitiator.

One embodiment of the present specification provides a photosensitive material comprising the photosensitive resin composition or a cured product.

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 composition comprising the compound according to an exemplary embodiment of the present specification may be used as a color material for a display cultivator filter. The color material composition of the present invention is excellent in transmittance and pattern formation, and is a new color material for color filters.

1 is a view showing a transmittance spectrum of a comparative example.
2 to 6 are diagrams showing transmittance spectra of Examples 1 to 5 including Compounds A to E according to one embodiment of the present specification.
7 is a diagram showing a pattern of a comparative example.
8 to 12 are diagrams showing patterns of Examples 1 to 5 including Compounds A to E according to one embodiment of the present specification.

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

According to an exemplary embodiment of the present specification, to provide a color material composition comprising a compound represented by the formula (1). When the compound represented by Chemical Formula 1 is used as a color material of the photosensitive resin composition, heat resistance and sensitivity can be improved.

The compound represented by Chemical Formula 1 is a compound having a structure in which an aromatic ring-N=cyclohexane substituted with a hydroxy group or an alkoxy group is connected, and the present inventors have found that performance is excellent when applied to a color filter of a photosensitive resin composition. The linkage of the aromatic ring-C-N=C-C-N=C-aromatic ring can shift the bandgap and shift the absorption spectrum through long conjugation. In addition, the hydroxy group increases the chemical bonding strength with other compositions to facilitate pattern formation of the photosensitive resin composition.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

는 연결되는 부위를 의미한다.In this specification,

Means the site to be connected.

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

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Sulfonic acid group; Sulfonate groups; Nitrile group; Nitro group; Hydroxy group; -COOH; Alkyl groups; Cycloalkyl group; Haloalkyl group; Alkenyl group; Amine group; Aryl group; Heteroaryl group; Acryloyl group; Acrylate groups; And one or more substituents selected from the group comprising a heterocyclic group containing one or more of N, O, or S atoms, or having no substituents.

According to an exemplary embodiment of the present specification, the "substituted or unsubstituted" is, deuterium; Halogen group; Sulfonic acid group; Sulfonate groups; Nitrile group; Nitro group; -COOH; Alkyl groups; Cycloalkyl group; Haloalkyl group; Amine group; Aryl group; And one or more substituents selected from the group containing heteroaryl groups.

According to an exemplary embodiment of the present specification, the "substituted or unsubstituted" is, deuterium; Halogen group; Nitro group; Alkyl groups; Aryl group; And one or more substituents selected from the group containing heteroaryl groups.

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

In one embodiment of the present specification, the sulfonate group may be represented by -SO ₃ M, and M may be any one of the Group 1 elements of the periodic table, for example, Na, but is not limited thereto.

In one embodiment of the present specification, the amine group is -NH ₂ ; -ND ₂ ; -NDH; Alkylamine groups; Cycloalkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but may be 1 to 30 days. In addition, it may be 1 to 20, and may be 1 to 10. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, cycloalkylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl -Anthracenylamine group, diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluorenylamine group and the like, but is not limited thereto.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. 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 are methyl group, 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 Tilgi, and the like, but are not limited to these.

In the present specification, the alkenyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 2 to 25. As a specific example, an alkenyl group substituted with an aryl group such as a stylbenyl group or a styrenyl group is preferred, but is not limited thereto.

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 cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20, and may be 6 to 10. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylene group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, and S. The number of carbon atoms is not particularly limited, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyridopyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthrolinyl group; Isooxazolyl group; Thiadiazolyl group; Phenothiazinyl group; And a dibenzofuranyl group, but is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.

In the present specification, the heterocycle is a non-carbon atom, and contains one or more heteroatoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is not monovalent.

In the present specification, the acryloyl group means a photopolymerizable unsaturated group, and examples thereof include (meth)acryloyl group, but are not limited thereto.

In the present specification, the acrylate group means a photopolymerizable unsaturated group, and examples thereof include (meth)acrylate groups, but are not limited thereto.

In the present specification,'(meth)acryloyl' refers to at least one selected from the group consisting of acryloyl and methacryloyl. The notation'(meth)acrylate' has the same meaning.

In the present specification, OAc means -O(C=O)CH ₃ , and-is a position connected to the compound.

In the present specification, NO ₃ means -ONO ₂ , and-is a position linked to a compound.

In the present specification, SO ₃ means -OSO ₂ , and-is a position linked to a compound.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or N(R1)(R2), or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms or N(R1)(R2), or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms or N(R1)(R2), or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring. In another exemplary embodiment, the "substituted or unsubstituted" is an alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms; And one or more substituents selected from the group containing a heteroaryl group having 2 to 20 carbon atoms or having no substituent.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; sec-butyl group; tert-butyl group; Methoxy group; Ethoxy group; Propoxyl; Isopropoxy group; Butoxy group; sec-butoxy group; tert-butoxy group; Phenyl group; Biphenyl group; Naphthyl group; Fluorenyl group; Dimethylfluorenyl group; Carbazole; Dibenzofuran group; Dibenzothiophene group; Pyridine group; Pyrimidine group; Dimethylamine group; Diethylamine group; Or a diphenylamine group, or adjacent substituents combine with each other to form a monocyclic or bicyclic ring.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; Methyl group; tert-butyl group; Phenyl group; Biphenyl group; Naphthyl group; Carbazole; Dibenzofuran group; Pyridine group; Diethylamine group; Or a diphenylamine group, or adjacent substituents combine with each other to form a monocyclic or bicyclic ring.

In one embodiment of the present specification, A1 and A3 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxy group; Methyl group; tert-butyl group; Phenyl group; Biphenyl group; Naphthyl group; Carbazole; Dibenzofuran group; Pyridine group; Diethylamine group; Or a diphenylamine group, or adjacent substituents combine with each other to form a monocyclic or bicyclic ring.

In one embodiment of the present specification, A1 and A3 are the same as or different from each other, and each independently hydrogen; Halogen group; tert-butyl group; Phenyl group; Naphthyl group; Or a dibenzofuran group, or adjacent substituents combine with each other to form a benzene ring.

In one embodiment of the present specification, A2 is hydrogen; Nitro group; Nitrile group; Methyl group; Or tert-butyl group.

In one embodiment of the present specification, A2 is hydrogen.

In one embodiment of the present specification, A1 and A3 are the same.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; A substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a heteroaryl group having 2 to 13 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Propyl group; tert-butyl group; Phenyl group; Naphthyl group; Biphenyl group; Fluorenyl group; Or a dimethylfluorenyl group.

In one embodiment of the present specification, R1 and R2 are ethyl groups; Or a phenyl group.

In one embodiment of the present specification, R1 and R2 are the same.

In one embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Propyl group; Butyl group; Or tert-butyl group.

In one embodiment of the present specification, R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl 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; Or a substituted or unsubstituted arylene 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; Or a substituted or unsubstituted monocyclic to 4 ring arylene 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; Or a substituted or unsubstituted arylene group having 6 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; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted fluorenylene 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; Or a substituted or unsubstituted monocyclic to bicyclic arylene 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; Or a phenylene group.

In one embodiment of the present specification, m1 is an integer from 0 to 6, and when 2 or more, L1-A1 are the same or different from each other.

In the exemplary embodiment of the present specification, m2 is an integer of 0 to 6, and when 2 or more, L2-A2 is the same or different from each other.

In one embodiment of the present specification, m3 is an integer of 0 to 10, and when 3 or more, A3 is the same or different from each other.

In one embodiment of the present specification, n1 and n2 are the same as or different from each other, and each independently an integer of 0 or 1.

In one embodiment of the present specification, m1 is 0, 1 or 2.

In one embodiment of the present specification, m2 is 0, 1, or 2.

In one embodiment of the present specification, m3 is 0 or 1.

In one embodiment of the present specification, m1 and m2 are the same.

및

은 서로 동일하거나 상이하다.In one embodiment of the present specification, Chemical Formula 1

And

Are the same or different from each other.

및

은 서로 동일하다.In one embodiment of the present specification, Chemical Formula 1

And

Are the same as each other.

및

은 서로 동일하거나 상이하다.In one embodiment of the present specification, Chemical Formula 1

And

Are the same or different from each other.

및

은 서로 동일하다.In one embodiment of the present specification, Chemical Formula 1

And

Are the same as each other.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,

The definitions of A1 to A3, R, R', L1, L2, m1 to m3, n1 and n2 are as defined in Formula 1.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3-1 to 3-3.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Chemical Formulas 3-1 to 3-3,

The definitions of A1 to A3, R, R', L1, L2, m1 to m3, n1 and n2 are as defined in Formula 1.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 4-1 to 4-8.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-8]

In Chemical Formulas 4-1 to 4-8,

A1 to A3, R, R', L1, L2 and m3 are defined as in Formula 1,

m11 is an integer from 0 to 4, and when 2 or more, L1-A1 are the same or different from each other,

m12 is an integer from 0 to 4, and when 2 or more, L2-A2 is the same or different from each other,

m13 is an integer from 0 to 6, when 2 or more, L1-A1 are the same or different from each other,

m14 is an integer from 0 to 4, and when 2 or more, L2-A2 is the same or different from each other,

m15 is an integer from 0 to 6, and when 2 or more, L1-A1 are the same or different from each other,

m16 is an integer of 0-6, and when it is 2 or more, L2-A2 is the same or different from each other.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any of the following Chemical Formulas, but is not limited thereto.

In addition, according to an exemplary embodiment of the present specification, to provide a color material composition comprising the compound.

The colorant composition may further include at least one of dyes and pigments in addition to the compound of Formula 1 above. For example, the colorant composition may include only the compound of Formula 1, but may include the compound of Formula 1 and one or more dyes, the compound of Formula 1 and one or more pigments, or the compound of Formula 1 , One or more dyes and one or more pigments.

According to an exemplary embodiment of the present specification, it is possible to provide a photosensitive resin composition comprising the color material composition.

According to an exemplary embodiment of the present specification, the photosensitive resin composition is a colorant composition comprising a compound represented by the formula (1); Binder resin; Polyfunctional monomers; And photoinitiators.

According to an exemplary embodiment of the present specification, the photosensitive resin composition is a colorant composition comprising a compound represented by the formula (1); Binder resin; Polyfunctional monomers; Photoinitiators; And solvents.

According to an exemplary embodiment of the present specification, the photosensitive resin composition further includes 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 a resin composition.

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

Polyfunctional monomers that impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And 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, and isobutyl ( Meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydrofuryl (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 CD ethylene 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) )Acrylates, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only these It is not limited.

Specific examples of the aromatic vinyls 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, but is not limited to these.

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 include N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.

Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, and tetrahydro phthalic anhydride, but are not limited thereto.

The monomer that gives the 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, 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 It is preferable to use one or more, but is not limited to these.

According to one embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOH mg/g, and the weight average molecular weight is 1,000 g/mol to 50,000 g/mol.

The acid value of the binder resin can be measured by titration with a 0.1 N concentration of potassium hydroxide (KOH) methanol solution.

The weight average molecular weight is a value obtained by averaging the molecular weights of the molecular weights of the component molecular species of the polymer compound having a molecular weight distribution as one of the average molecular weights in which the molecular weight is not uniform and the molecular weight of a certain polymer material is used as a standard.

The weight average molecular weight can be measured through Gel Permeation Chromatography (GPC) analysis.

According to an exemplary embodiment of the present specification, the binder resin is a copolymer of a monomer containing an unsaturated carboxylic acid ester and an acid group.

According to an exemplary embodiment of the present specification, the binder resin is a copolymer of benzyl methacrylate and methacrylic acid.

The polyfunctional monomer is a monomer that serves to form a photoresist phase 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 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate It may be a species or a mixture of two or more.

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

The acetophenone-based compounds are 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-hydroxycyclohexylphenylketone, benzoinmethyl ether, benzoinethyl ether, benzoinisobutyl 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, but is not limited thereto.

The biimidazole-based compound is 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 is not limited to this.

The triazine-based compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-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-triazine-6 -Yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazine-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-triazine-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.

The oxime-based compound is 1,2-octadione,-1-(4-phenylthio)phenyl,-2-(o-benzoyloxime) (Shibagai, Shijii124), ethanone,-1-(9 -Ethyl)-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime) (CG 242), N-1919 (Adeka), and the like.

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 one or more 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 1% to 60% by weight, the content of the binder resin is 1% by weight To 80% by weight, the content of the photoinitiator is 0.1% to 20% by weight, and the content of the multifunctional monomer is 0.1% to 50% by weight.

According to an exemplary embodiment of the present specification, based on the total weight of 100 parts by weight of the solid content in the photosensitive resin composition, the content of the compound represented by Formula 1 is 1% to 60% by weight; 3% to 30% by weight; 5% to 20% by weight; Or 6% to 10% by weight.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The basis of the solid content and the weight percent 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.

According to an exemplary embodiment of the present specification. The photosensitive resin composition may further include a surfactant.

According to an exemplary embodiment of the present specification, the photosensitive resin composition is 1 or 2 selected from the group consisting of photo-crosslinking agent, curing accelerator, adhesion promoter, surfactant, thermal polymerization inhibitor, antioxidant, ultraviolet absorber, dispersant and leveling agent The above additives are further included.

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

The photocrosslinking agent 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, 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Florenone-based compounds, such as 9-Florenone, 2-Croro-9-Prorenone, and 2-methyl-9-Florenone; Thioxanthone series such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; Xanthone 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 compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptan-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]-quinolinazine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azide benzal acetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of;

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

As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more of meta acryloyl silane coupling agents can be selected and used. As the alkyl trimethoxy silane, at least one of octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane can be used. You can choose and use.

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-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, etc. can be used. DIC is a fluorine-based surfactant (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, trimethylphosphate or triethylphosphate; 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 esters, such as hindered phenol-based primary antioxidants; 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, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuramdisulfide tetrabis[methylene-3-(laurylthio)propionate]methane Secondary antioxidants; Or triphenyl phosphite, tris(nonylphenyl)phosphite, triisodecylphosphite, 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' And phosphite-based secondary antioxidants such as -Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester).

As the ultraviolet absorber, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto, and in the art Anything commonly used can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but are not limited to these, and the sugar technology These may include those commonly 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 treatment in advance, or a method of externally adding to the pigment. As the dispersing agent, a compound type, nonionic, anionic or cationic dispersing agent may be used, and examples thereof include fluorine-based, ester-based, cationic-based, anionic-based, non-ionic and amphoteric surfactants. These may be used individually or in combination of two or more.

Specifically, the dispersant is polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, There is at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.

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

According to an exemplary embodiment of the present specification, to provide a prepared photosensitive material comprising the photosensitive resin composition or a cured product thereof.

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

Although the coating method is not particularly limited, a spray method, a roll coating method, a spin coating method, or the like can be used, and the spin coating method is generally widely used. In addition, after forming the coating film, in some cases, the residual solvent may be partially removed under reduced pressure.

As a light source for curing the resin composition according to the present specification, for example, there is a mercury vapor arc (arc), carbon arc, Xe arc, etc. that emits light having a wavelength of 250 nm to 450 nm, but is not limited thereto.

The resin composition according to the present specification is a thin film transistor type liquid crystal display (TFT LCD) pigment dispersion type photosensitive material for manufacturing a 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, It can be used for photoresist for overcoat layer formation, column spacer photoresist, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. It is not specially placed.

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

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

The resin composition according to an exemplary embodiment of the present specification is excellent in heat resistance, and the color change due to heat treatment is small, and thus a color filter having high color reproducibility and excellent sensitivity can be provided even by a curing process in the production of a color filter.

The substrate may be a glass plate, a silicon wafer, and a plastic-based plate 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 black pattern on a grid called a black matrix may be disposed between color pixels of the color filter for the purpose of improving contrast. Chrome 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, considering the high cost in the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present specification may use a black pigment or black dye as a color material. For example, carbon black may be used alone, or a mixture of carbon black and a coloring pigment may be used. In this case, since the coloring pigment having insufficient light-shielding property is mixed, the strength of the film or the adhesion to the substrate decreases even when the amount of the coloring material is relatively increased. It has the advantage of not being.

According to one embodiment of the present specification, a display device including the color filter 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), a thin film transistor It may be any one of a liquid crystal display (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

<Production Example>

Preparation Example 1 Synthesis of Compound A

Cyclohexane-1,2-diamine (5.0 g, 43.8 mmol) and 2-hydroxy-1-naphthalaldehyde (16.6 g, 96.4 mmol) were added with ethanol (100 ml) and stirred at about 60° C. for 6 hours. . After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound A (14.42 g, 78%): MS [M] = 422.2

Preparation Example 2: Synthesis of Compound B

1. Synthesis of Compound B-1

Cyclohexane-1,2-diamine (5.0 g, 43.8 mmol) was dissolved in ethanol (30 ml) and then stirred at room temperature for 10 minutes. 2-Hydroxy-1-naphthalaldehyde (7.5 g, 43.8 mmol) was dissolved in ethanol (50 ml), slowly added dropwise, stirred at room temperature for 4 hours, and filtered. After the reaction was completed, after filtering, the filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound B-1 (9.5 g, 81%): MS [M] = 268.16

2. Synthesis of Compound B

Compound B-1 (5.0 g, 18.6 mmol) and 3,5-di-tert-butyl-2-hydroxybenzaldehyde (4.5 g, 19.2 mmol) were added with ethanol (100 ml) and stirred at about 60° C. for 6 hours. Ordered. After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound B (7.75 g, 86%): MS [M] = 484.3

Preparation Example 3: Synthesis of Compound C

1. Synthesis of Compound C-1

5-bromo-2-hydroxybenzaldehyde (5.0 g, 25.0 mmol) and naphthalen-2-yl boronic acid (5.2 g, 30.0 mmol) and Pd(t-Bu ₃ P) ₂ (0.038 g, 0.075 mmol) Into 2M K ₂ CO ₃ aqueous solution (30 mL) and tetrahydrofuran (THF) (200 mL), and stirred at reflux for about 4 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, and distilled under reduced pressure, and recrystallized with ethyl acetate/hexane to obtain compound C-1 (4.84 g, 78%): MS [ M] = 248.08

2. Synthesis of Compound C-2

Cyclohexane-1,2-diamine (5.0 g, 43.82 mmol) was dissolved in ethanol (30 ml) and then stirred at room temperature for 10 minutes. Compound C-1 (10.3 g, 41.62 mmol) was dissolved in ethanol (50 ml), slowly added dropwise, stirred at room temperature for 4 hours, and filtered. After the reaction was completed, after filtering, the filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound C-2 (11.6 g, 81%): MS [M] = 344.19

3. Synthesis of Compound C

Compound C-2 (5.0 g, 14.53 mmol) and 6-bromo-2-hydroxy-1-naphthalaldehyde (3.74 g, 14.96 mmol) were added with ethanol (100 ml) and stirred at about 60° C. for 6 hours. . After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound C (7.0 g, 84%): MS [M] = 576.14

Preparation Example 4 Synthesis of Compound D

1. Synthesis of Compound D-1

5-bromo-2-hydroxybenzaldehyde (5.0 g, 25.0 mmol) and dibenzo[b,d]furan-2-yl boronic acid (6.4 g, 30.0 mmol) and Pd(t-Bu ₃ P) ₂ (0.038 g, 0.075 mmol) was added to a 2M K ₂ CO ₃ aqueous solution (30 mL) and tetrahydrofuran (THF) (200 mL), and the mixture was stirred at reflux for about 4 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, and distilled under reduced pressure and recrystallized from ethyl acetate/hexane to obtain compound D-1 (5.69 g, 79%): MS [ M] = 288.08

2. Synthesis of Compound D-2

Cyclohexane-1,2-diamine (5.0 g, 43.82 mmol) was dissolved in ethanol (30 ml) and then stirred at room temperature for 10 minutes. Compound D-1 (12.0 g, 41.62 mmol) was dissolved in ethanol (50 ml), slowly added dropwise, stirred at room temperature for 4 hours, and filtered. After the reaction was completed, after filtering, the filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound D-2 (13.6 g, 85%). MS [M] = 384.18

3. Synthesis of Compound D

Compound D-2 (5.0 g, 13.0 mmol) and 6-bromo-2-hydroxy-1-naphthalaldehyde (3.35 g, 13.4 mmol) were added with ethanol (100 ml) and stirred at about 60° C. for 6 hours. . After the reaction was completed, it was cooled to room temperature and filtered. The filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, filtered again, and dried to obtain compound D (6.89 g, 86%): MS [M] = 616.14

Preparation Example 5 Synthesis of Compound E

1. Synthesis of Compound E-1

5-bromo-2-hydroxybenzaldehyde (5.0 g, 20.0 mmol) and (4-(tert-butyl)phenyl)boronic acid (5.34 g, 30.0 mmol) and Pd(t-Bu ₃ P) ₂ (0.038 g, 0.075 mmol) was added to a 2M K ₂ CO ₃ aqueous solution (30 mL) and tetrahydrofuran (THF) (200 mL), and the mixture was stirred at reflux for about 4 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, and distilled under reduced pressure, and recrystallized with ethyl acetate/hexane to obtain compound E-1 (5.35 g, 88%): MS [ M] = 304.15

2. Synthesis of Compound E

Cyclohexane-1,2-diamine (5.0 g, 43.82 mmol) was dissolved in ethanol (30 ml) and then stirred at room temperature for 10 minutes. Compound E-1 (28.0 g, 92.0 mmol) was dissolved in ethanol (50 ml), then slowly added dropwise, stirred at room temperature for 4 hours, and filtered. After the reaction was completed, after filtering, the filtrate was collected, placed in distilled water (50 ml), stirred at room temperature for 30 minutes, and then filtered again. The filtrate was dried to give compound E (26.5 g, 88%): MS [M] = 686.39

<Product composition>

Example-1

Colorant composition containing 3.000 g of Compound A, 29.480 g of binder resin, 2.000 g of photoinitiator (Igacure-369), multifunctional monomer (photopolymerizable compound, DPHA (Japanese Chemicals)) 7.370 g, solvent (propylene glycol monomethyl ether acetate (PGMEA)) A photosensitive resin composition was prepared by mixing 17.650 g and 40.000 g of DMF (dimethylformamide) and 1.016 g of an additive (surfactant, F-475 from DIC).

The binder resin is a copolymer of benzyl methacrylate and methacrylic acid, the molar ratio of benzyl methacrylate and methacrylic acid is 70:30, and the acid value is 80 KOH mg/g. The weight average molecular weight measured by GPC is 12,000 g/mol, and the molecular weight distribution (PDI) is 2.0 g. Propylene glycol monomethyl ether acetate (PGMEA) was used in 25 parts by weight of solids (S.C.).

Example-2 to Example-5

A photosensitive resin composition was prepared in the same manner as in Example-1, except that Compounds B to E were used instead of Compound A in Example-1.

Comparative example

A photosensitive resin composition was prepared in the same manner as in Example-1, except that the following Compound Pigment Y 138 was used instead of Compound A in Example-1. Pigment Y 138 is a compound used in the art as a yellow colorant for color filters.

<Experimental Example>

Substrate production

The photosensitive resin compositions of Examples 1 to 5 and Comparative Examples were used for substrate production, respectively. Specifically, the photosensitive resin compositions of Examples 1 to 5 and Comparative Examples were spin coated on glass (5 X 5 cm), and then subjected to prebake (PrB) at 100° C. for 100 seconds. A film was formed.

The distance between the substrate on which the film was formed and the photomask was set to 300 μm, and an exposure dose of 40 mJ/cm ² was investigated on the entire surface of the substrate using an exposure machine. The photomask is made of quartz.

Thereafter, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and the exposed substrate was subjected to post-heat treatment (postbake; PB) at 230°C for 20 minutes.

Transmittance evaluation

After the post-heat treatment, the transmittance spectrum of the visible light region (380 nm-780 nm) for Comparative Examples and Examples 1 to 5 was measured using a spectrophotometer, and the results are shown in FIGS. 1 to 6. 1 shows the transmittance spectrum of the comparative example, and FIGS. 2 to 6 show the transmittance spectrum of Examples 1 to 5.

Pigment Y 138 used in the comparative example is a material used in the art as a yellow color material for color filters. The present inventors apply the compound represented by Formula 1 to a color material for a color filter, and as a result, Examples 1 to 5 (FIGS. 2 to 6) show comparative examples in the yellow wavelength range of 570 nm to 590 nm (FIG. It was found that the transmittance was as high as 1). In addition, in the short wavelength band, Examples 1 to 5 show higher transmittance than Comparative Examples, so it is easy to control the intensity of colors and the like.

Therefore, it can be seen that the colorant composition of the present invention can be used as a yellow colorant.

Solubility evaluation

The prepared comparative examples and compositions of Examples 1 to 5 were measured for solubility based on propylene glycol methyl ether acetate (PGMEA), and the results are shown in Table 1 below.

Solubility (%) Comparative example <0.1 Example-1 0.3 Example-2 1.2 Example-3 0.8 Example-4 <0.1 Example-5 3.6

Referring to Table 1, the solubility values of Examples 1 to 5 in which the compound represented by Chemical Formula 1 was applied to a color material for a color filter is higher than the solubility values of Comparative Examples used in the art.

Therefore, it can be seen that the colorant composition of the present invention has excellent solubility in a solvent. The colorant composition of the present invention can be utilized as a soluble colorant, that is, a dye, and can be used together with an insoluble colorant to express various colors as a display colorant.

Formation pattern evaluation

The formed pattern was measured using an optical microscope (X20) and displayed in FIGS. 7 to 12. Fig. 7 shows the pattern of the comparative example, and Figs. 8 to 12 show the patterns of Examples-1 to 5.

The patterns of Examples 1 to 5 (FIGS. 8 to 12) in which the compound represented by Chemical Formula 1 is applied to a color material for a color filter are formed as smoothly as the comparative examples (FIG. 7) used in the art. do.

Therefore, it can be seen that the color material composition of the present invention has excellent pattern forming characteristics when used as a color filter.

Claims (14)

Colorant composition comprising a compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or N(R1)(R2), or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
R and R'are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
m1 is an integer from 0 to 6, and when 2 or more, L1-A1 are the same or different from each other,
m2 is an integer from 0 to 6, and when 2 or more, L2-A2 is the same or different from each other,
m3 is an integer from 0 to 10, and when 2 or more, A3 is the same or different from each other,
n1 and n2 are the same as or different from each other, and each independently an integer of 0 or 1. The method according to claim 1, wherein the formula 1 is a colorant composition represented by the following formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,
The definitions of A1 to A3, R, R', L1, L2, m1 to m3, n1 and n2 are as defined in Formula 1. The method according to claim 1, wherein the formula 1 is a colorant composition represented by any one of the following formulas 3-1 to 3-3:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Chemical Formulas 3-1 to 3-3,
The definitions of A1 to A3, R, R', L1, L2, m1 to m3, n1 and n2 are as defined in Formula 1. The method according to claim 1, wherein the formula 1 is a colorant composition represented by any one of the following formulas 4-1 to 4-8:
[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-8]

In Chemical Formulas 4-1 to 4-8,
A1 to A3, R, R', L1, L2 and m3 are defined as in Formula 1,
m11 is an integer from 0 to 4, and when 2 or more, L1-A1 are the same or different from each other,
m12 is an integer from 0 to 4, and when 2 or more, L2-A2 is the same or different from each other,
m13 is an integer from 0 to 6, when 2 or more, L1-A1 are the same or different from each other,
m14 is an integer from 0 to 4, and when 2 or more, L2-A2 is the same or different from each other,
m15 is an integer from 0 to 6, and when 2 or more, L1-A1 are the same or different from each other,
m16 is an integer of 0-6, and when it is 2 or more, L2-A2 is the same or different from each other. The method according to claim 1,
A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitro group; Nitrile group; Halogen group; Hydroxy group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or N(R1)(R2), or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl material having 6 to 20 carbon atoms. The method according to claim 1,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a phenylene group colorant composition. The method according to claim 1,
R and R'are the same as or different from each other, and hydrogen; heavy hydrogen; Or a methyl material colorant composition. The method according to claim 1, wherein the compound represented by Formula 1 is a colorant composition represented by any one of the following compounds:

. The color material composition of any one of claims 1 to 8; Binder resin; Polyfunctional monomers; And a photoinitiator. The method according to claim 9, The content of the compound represented by Formula 1 based on the total weight of solids in the photosensitive resin composition is 1% to 60% by weight,
The content of the binder resin is 1% by weight to 80% by weight,
The content of the photoinitiator is 0.1% to 20% by weight,
The content of the polyfunctional monomer is 0.1 to 50% by weight of the photosensitive resin composition. The photosensitive resin composition of claim 9, further comprising a solvent. A photosensitive material comprising the photosensitive resin composition according to claim 9 or a cured product thereof. A color filter comprising the photosensitive material according to claim 12. Display device comprising a color filter according to claim 13.

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