CN109312170B - Compound and photosensitive resin composition comprising the same - Google Patents

Abstract

The present invention relates to a compound having a novel chemical structure and a photosensitive resin composition comprising the same, and a photosensitive material, a color filter and a display device manufactured by using the same.

Description

Compound and photosensitive resin composition comprising the same

Technical Field

Cross Reference to Related Applications

This application claims the benefit of priority from korean patent application No. 10-2017-0048106, filed on 13/4/2017, the entire disclosure of which is incorporated herein by reference.

The present invention relates to a compound, a photosensitive resin composition comprising the same, and a photosensitive material, a color filter and a display device manufactured by using the same. More particularly, the present invention relates to a compound having excellent color characteristics, heat resistance and solvent resistance; a photosensitive resin composition using the same; and a photosensitive material, a color filter and a display device manufactured by using the same.

Background

For the present color filter, performance characteristics including high luminance and high contrast are required. Further, one of the main purposes of developing a display device is to distinguish the performance of the display device by improving color purity and to improve productivity in the manufacturing process.

Since the pigment type used as a color material of the existing color filter exists in the color photoresist in a state in which particles are dispersed, there is a difficulty in adjusting brightness and contrast by adjusting the size and distribution of pigment particles. In the case of pigment particles, the particles are aggregated in the color filter, the dissolution property and dispersion property are degraded due to large particles that have been aggregated, and much light scattering occurs. Scattering of this polarized light is considered to be a major factor in reducing the contrast.

Therefore, studies have been made to improve brightness and contrast by ultrafine particle formation and dispersion stabilization of pigments, but the degree of freedom in selection of color materials for realizing color coordinates of high color purity display devices is limited.

In addition, a pigment dispersion method using color materials, particularly pigments, has been developed to reach the limit of improving color purity, brightness and contrast of a color filter using the method.

Therefore, development of new color materials capable of improving color reproduction, brightness, and contrast by increasing color purity is required.

Disclosure of Invention

Technical problem

An object of the present invention is to provide a compound having excellent color characteristics, heat resistance and solvent resistance.

It is another object of the present invention to provide a photosensitive resin composition using the above compound.

It is still another object of the present invention to provide a color filter and a display device manufactured by using the above compound or photosensitive resin composition.

Technical scheme

The present specification provides a compound represented by chemical formula 1.

The present specification also provides a color material composition comprising the above compound.

Further, the present specification provides a photosensitive resin composition comprising the compound or the color material composition.

The present specification also provides a photosensitive material manufactured by using the photosensitive resin composition and a color filter or display device using the photosensitive material.

Hereinafter, compounds according to embodiments of the present invention and photosensitive resin compositions comprising the same will be described in more detail.

Throughout this specification, when a portion "includes" one constituent element, unless specifically described otherwise, this does not mean that another constituent element is excluded, but means that another constituent element may be further included.

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

As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and a position to be substituted is not limited as long as the position is a position at which the hydrogen atom is substituted, that is, a position at which the substituent may be substituted, and when two or more are substituted, two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a carboxyl group, a sulfonic group, a sulfonamide group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an arylphosphino group, or a heterocyclic group containing at least one of N, O and S atoms, or no substituent, or a substituent in which two or more substituents among exemplary substituents are linked, or no substituent. For example, the term "a substituent in which two or more substituents are linked" may refer to a biphenyl group. That is, biphenyl may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are linked.

In the context of the present specification,

or-means a bond to another substituent, and a single bond means the case where another atom is not present in the moiety represented by L.

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

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the imide group may be a compound having the following structure, but is not limited thereto.

In the present specification, in the amide group, the nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, the amide group may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 30. Specifically, the carbonyl group may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may have the following structure: wherein the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structure, but is not limited thereto.

In the present specification, the sulfonamido group may be-SO₂NR 'R ", wherein R' and R" are the same or different from each other and may each be independently selected from hydrogen, deuterium, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl 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.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methoxy group, ethoxy group, n-propoxy group, isopropoxy group (isopropoxy group), isopropoxy group (i-propyloxy group), n-butoxy group, isobutoxy group, t-butoxy group, sec-butoxy group, n-pentoxy group, neopentoxy group, isopentoxy group, n-hexoxy group, 3-dimethylbutoxy group, 2-ethylbutoxy group, n-octoxy group, n-nonoxy group, n-decoxy group, benzyloxy group, p-methylbenzyloxy group and the like, but are not limited thereto.

In the present specification, the amine group may be selected from-NH₂Monoalkylamino group, dialkylamino group, N-alkylarylamino group, monoarylamino group, diarylamino group, N-arylheteroarylamino group, N-alkylheteroarylamino group, monoheteroarylamino group, and diheteroarylamino group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a ditolylamino group, an N-biphenylnaphthylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenyltriphenylamino group, an N-phenanthrylfluorenylamino group, an N-biphenylfluorenylamino group, and the like.

In the present specification, an N-alkylarylamino group means an amino group in which N of the amino group is substituted with an alkyl group and an aryl group.

In the present specification, N-arylheteroarylamino means an amino group in which N of the amino group is substituted with aryl and heteroaryl groups.

In the present specification, N-alkylheteroarylamino means an amino group in which N of the amino group is substituted with alkyl and heteroarylamino groups.

In the present specification, the alkyl group in the monoalkylamino group, dialkylamino group, N-arylalkylamino group, alkylthio group, alkylsulfonyl group and N-alkylheteroarylamino group is the same as the example of the above-mentioned alkyl group. Specifically, examples of the alkylthio group include methylthio, ethylthio, tert-butylthio, hexylthio, octylthio and the like, and examples of the alkylsulfonyl group include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and the like, but examples thereof are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.

In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.

In the present specification, specific examples of the phosphine oxide group include, but are not limited to, diphenylphosphineoxide, dinaphthylphospheoxide, and the like.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, the aryl group may be, but is not limited to, phenyl, biphenyl, terphenyl, and the like. Examples of polycyclic aromatic groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, perylene,

A phenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present specification, a fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro structure. In the case of substituted fluorenyl radicals, may form

And the like. However, the structure is not limited thereto.

In the present specification, an "adjacent" group may be a substituent substituted with an atom directly bonded to an atom substituted with the corresponding substituent, a substituent disposed closest to the corresponding substituent in space, or another substituent substituted for an atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position of the phenyl ring and two substituents substituted for the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.

In the present specification, the aryl group in the monoarylamino group, diarylamino group, aryloxy group, arylthio group, arylsulfonyl group, N-arylalkylamino group, N-arylheteroarylamino group, and arylphosphino group is the same as the example of the above-mentioned aryl group. Specifically, examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3, 5-dimethyl-phenoxy group, 2,4, 6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenyloxy group, 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthrenyloxy group, 3-phenanthrenyloxy group, 9-phenanthrenyloxy group and the like, examples of the arylthio group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfonyl group include benzenesulfonyl, p-toluenesulfonyl and the like, but examples thereof are not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Se and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolylQuinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazoleBasic group, hetero

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, aziridinyl, azaindolyl, isoindolyl, indazolyl, purinyl, pteridinyl, β -carbolinyl, naphthyridinyl, terpyridinyl, phenazinyl, imidazopyridinyl, pyropyridine (pyropyradyl), azepinyl, pyrazolyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, examples of heteroaryl groups in the monoheteroarylamino group, diheteroarylamino group, N-arylheteroarylamino group and N-alkylheteroarylamino group may be selected from the above-mentioned examples of heteroaryl groups.

In the present specification, the alkylene group is a divalent functional group derived from an alkane, and examples thereof include a linear, branched or cyclic group such as methylene, ethylene, propylene, isobutylene, sec-butyl ene, tert-butyl ene, pentylene, hexylene and the like.

In the present specification, haloalkylene means a functional group in which the above alkylene group is substituted with a halogen group, for example, perfluoropropane-2, 2-diyl and the like.

In the present specification, arylene means that two bonding positions, i.e., divalent groups, are present in an aryl group. The above description of aryl groups can be applied with the difference that the arylene groups are each divalent groups.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from examples of the cycloalkyl group or the aryl group, except that the hydrocarbon ring is not 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 the aromatic ring is not monovalent.

In the present specification, the heterocyclic ring contains one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The heterocyclic ring may be monocyclic or polycyclic, may be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring, and may be selected from examples of the heteroaryl group except that the heterocyclic ring is not monovalent.

In the present specification, "direct bond" means a bond to a bonding wire, wherein no atom or group of atoms is present at the corresponding position.

According to an embodiment of the present invention, there may be provided a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1, the first and second,

y1 and Y2 are the same or different from each other and are each independently a direct bond or-CQ 1Q 2-;

a is a direct bond, an ether group, a carbonyl group, an ester group, a diester group, a peroxy group, an amino group, an imino group, an imide group, an azo group, an amide group, a sulfone group, an alkylene group having 1 to 10 carbon atoms, a heteroalkylene group having 1 to 10 carbon atoms, a halogenated alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms,

r1 to R26, Q1 and Q2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a carboxyl group (-COOH), -OC (═ O) R' ", a sulfonic acid group (-SO)₃H) Sulfonamide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstitutedA substituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups may be connected to each other to form a substituted or unsubstituted ring, and

r' "is a substituted or unsubstituted alkyl group.

The present inventors found through experiments that, since the solubility of a compound in a solvent is increased by a sulfonate group included in a molecular structure as shown in chemical formula 1, reaggregation of the compound can be prevented and the formation of foreign substances can be suppressed, and thus color purity, brightness, and contrast can be improved when applied to a color filter, thereby completing the present invention.

In particular, in the compound of one embodiment, two sulfonic acid groups are introduced into the molecular structure due to the formation of the dimer, so that the effect of improving solubility by the sulfonate group can be further enhanced, and furthermore, the spectrum emitted from the light source and the absorption spectrum and the transmission spectrum of the color filter are appropriately combined, so that the color purity is increased and the color reproduction, the brightness, and the contrast can be improved. In addition, heat resistance is improved due to an increase in molecular weight, and abrupt changes in color purity, brightness, and contrast do not occur even after a heat treatment step when a photosensitive material is manufactured, thereby achieving stable display performance.

Further, since the compound of one embodiment employs an aromatic functional group bonded to the terminal of the sulfonate group, for example, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, an effect of improving heat resistance can be achieved.

Specifically, in chemical formula 1, Y1 and Y2 are the same as or different from each other, and are independently a direct bond or — CQ1Q 2-. in-CQ 1Q2-, C is carbon, and Q1 and Q2 may represent functional groups each independently bonded to carbon. Thus, when Y1 or Y2 is a direct bond, a pentagonal ring having 5 carbon atoms may be formed, and when Y1 or Y2 is-CQ 1Q2-, a hexagonal ring having 6 carbon atoms may be formed.

Further, in chemical formula 1, a is a direct bond, an ether group, a carbonyl group, an ester group, a diester group, a peroxy group, an amino group, an imino group, an imide group, an azo group, an amide group, a sulfone group, an alkylene group having 1 to 10 carbon atoms, a heteroalkylene group having 1 to 10 carbon atoms, a haloalkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.

More preferably, in chemical formula 1, a may be a direct bond, an ether group, a carbonyl group, a diester group, a sulfone group, an alkylene group having 1 to 10 carbon atoms, or a haloalkylene group having 1 to 10 carbon atoms.

The diester group is a functional group including two ester functional groups, and examples thereof include a functional group represented by the following chemical formula 2.

[ chemical formula 2]

In chemical formula 2, X is an alkylene group having 1 to 10 carbon atoms, a heteroalkylene group having 1 to 10 carbon atoms, a haloalkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms. Preferably, X may be an alkylene group having 1 to 5 carbon atoms, such as methylene, ethylene, propylene, and the like.

The haloalkylene group having 1 to 10 carbon atoms means a functional group in which an alkylene group having 1 to 10 carbon atoms is substituted with a halogen group, and examples thereof include perfluoropropane-2, 2-diyl and the like.

In chemical formula 1, R1 to R26 are the same as or different from each other, and are each independently hydrogen, a halogen group, a nitro group, a carboxyl group, an ester group, a hydroxyl group, -OC (═ O) R' ", a sulfonic acid group (-SO)₃H) Substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstitutedSubstituted or unsubstituted aryl groups, or adjacent groups may be linked to each other to form a substituted or unsubstituted ring.

R' "is substituted or unsubstituted alkyl.

R' "is methyl.

In chemical formula 1, R1 to R26 are the same as or different from each other, and are independently hydrogen, fluorine, chlorine, bromine, iodine, nitro, carboxyl, alkyl ester group, cycloalkyl ester group, arylalkyl ester group, hydroxyl, -OC (═ O) CH₃Sulfonic acid group (-SO)₃H) Methyl, tert-butyl, methoxy, phenyl or naphthyl.

In chemical formula 1, at least one of Q1, Q2, and R17 to R26 may be combined with an adjacent functional group to form a substituted or unsubstituted aromatic ring.

Specifically, in chemical formula 1, at least one of Q1, Q2, and R17 to R26 is combined with an adjacent functional group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

In chemical formula 1, Y1 and Y2 may each independently be a direct bond.

The compound of one embodiment may be represented by the following chemical formula 1-1.

[ chemical formula 1-1]

In the chemical formula 1-1,

a is a direct bond, an ether group, a carbonyl group, a diester group, a sulfone group, an alkylene group having 1 to 10 carbon atoms, or a halogenated alkylene group having 1 to 10 carbon atoms, and R27 and R28 are the same as or different from each other and are each independently a phenyl group or a naphthyl group.

Further, the compound of one embodiment may be represented by the following chemical formula 1-2 or 1-3.

[ chemical formulas 1-2]

[ chemical formulas 1-3]

In chemical formula 1-2 or 1-3, a is a direct bond, an ether group, a carbonyl group, a diester group, a sulfone group, an alkylene group having 1 to 10 carbon atoms, or a halogenated alkylene group having 1 to 10 carbon atoms, and R28 to R31 are the same or different from each other and are each independently a phenyl group or a naphthyl group.

The compound of one embodiment may be represented by any one of the following chemical formulas 1-4 to 1-15.

[ chemical formulas 1 to 4]

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

[ chemical formulas 1 to 7]

[ chemical formulas 1 to 8]

[ chemical formulas 1 to 9]

[ chemical formulas 1-10]

[ chemical formulas 1 to 11]

[ chemical formulas 1 to 12]

[ chemical formulas 1 to 13]

[ chemical formulas 1 to 14]

[ chemical formulas 1 to 15]

Meanwhile, according to another embodiment of the present invention, a color material composition including the compound of the above-described one embodiment may be provided.

Details of the above compounds include those described above with respect to one embodiment.

The color material composition may further include at least one of a dye and a pigment. For example, the above color material composition may contain only the compound of one embodiment described above, but it may contain the compound of one embodiment and one or more dyes, or may contain the compound of one embodiment and one or more pigments, or may contain the compound of one embodiment and one or more dyes and one or more pigments.

The specific kind of the dye or pigment used herein is not particularly limited, and various materials widely used in the field of color filters or displays may be used without limitation.

Meanwhile, according to another embodiment of the present invention, there may be provided a photosensitive resin composition comprising the compound of the above-described one embodiment or the color material composition of the above-described other embodiments, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

Details of the above compounds include those described above with respect to one embodiment, and details of the color material composition include those described above with respect to other embodiments.

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

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

The multifunctional monomer that imparts mechanical strength to the film may be at least one of an unsaturated carboxylic acid ester, an aromatic vinyl group, an unsaturated ether, an unsaturated imide, and an acid anhydride.

Specific examples of the unsaturated carboxylic acid ester may be selected from benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, tert-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-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiglycol (meth) acrylate, methoxytriglycol (meth) acrylate, methoxypropylpropylene (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxyethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1, 3-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 3535, α, 3-fluoroethylpropyl (meth) acrylate, 3-2-hydroxytribromo, 3-2-hydroxytribromo.

Specific examples of the aromatic vinyl monomer may be selected from styrene, α -methylstyrene, (o, m, p) -vinyltoluenes, (o, m, p) -methoxystyrenes, and (o, m, p) -chlorostyrenes, but are not limited thereto.

Specific examples of the unsaturated ether 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 imide may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide, but are not limited thereto.

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

The monomer imparting alkali solubility is not particularly limited as long as it contains an acid group, and for example, at least one selected from the group consisting of: (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, and ω -carboxy polycaprolactone mono (meth) acrylate, but are not limited thereto.

According to one embodiment of the present invention, the acid value of the binder resin is 50KOH mg/g to 130KOH mg/g, and the weight average molecular weight is 1000 to 50000.

The polyfunctional monomer is a monomer having an effect of forming a photoresist image by light, and specific examples thereof include one or a mixture of two or more selected from the group consisting of: propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1, 6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxyethylene diacrylate, trihydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals to initiate crosslinking upon exposure to light. For example, the photoinitiator may be at least one selected from the group consisting of: acetophenone compounds, non-imidazole compounds, triazine compounds and oxime compounds.

The acetophenone compound may be at least one selected from the group consisting of: 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) one, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholin-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butan-1-one, methyl-2-hydroxy-2-methyl-2-phenylpropan-1-one, methyl-2-hydroxy-2-methyl-2-propyl-ketone, methyl-2-hydroxy-1-methyl-1-one, methyl-2-morpholinyl-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, and the like, but is not limited thereto.

The non-imidazole compound may be at least one selected from the group consisting of: 2,2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetraphenyl non-imidazole, 2' -bis (o-chlorophenyl) -4,4 ', 5, 5' -tetrakis (3,4, 5-trimethoxyphenyl) -1,2 '-non-imidazole, 2' -bis (2, 3-dichlorophenyl) -4,4 ', 5, 5' -tetraphenyl non-imidazole, 2 '-bis (o-chlorophenyl) -4, 4', 5,5 '-tetraphenyl-1, 2' -non-imidazole, and the like, but is not limited thereto.

The triazine compound may be at least one selected from the group consisting of: 3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 1,1,3,3, 3-hexafluoroisopropyl-3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoate/salt, ethyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate/salt, 2-epoxyethyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate/salt, cyclohexyl 2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate/salt, benzyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate/salt, 3- (chloro-4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanamide, 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, but is not limited thereto.

The oxime compound may be at least one selected from the group consisting of: 1, 2-octanedione-1- (4-phenylthio) phenyl-2- (phthaloyl oxime) (CGI 124, manufactured by Ciba-Geigy), ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (O-acetyl oxime) (CGI 242, manufactured by Ciba-Geigy) and N-1919 (manufactured by Adeka Corp.).

The solvent may be at least one selected from the group consisting of: acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1, 4-bis

Alkane, 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-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl-3-ethoxybutyl acetatePropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but are not limited thereto.

The content of the compound may be 5 to 60% by weight based on the total weight of the solids in the photosensitive resin composition. In addition, the content of the binder resin may be 1 to 60% by weight, the content of the photoinitiator may be 0.1 to 20% by weight, and the content of the multifunctional monomer may be 0.1 to 50% by weight.

The total weight of solids means the sum of the total weight of components other than the solvent in the resin composition. The standard based on the weight% of solid content and the solid content of each component can be measured by a conventional analytical method used in the art such as liquid chromatography or gas chromatography.

In addition, the photosensitive resin composition may further include an antioxidant. The antioxidant is contained in an amount of 0.1 to 20% by weight, based on the total weight of solids in the photosensitive resin composition.

The antioxidant may be at least one selected from the group consisting of: hindered phenol-based antioxidants, amine-based antioxidants, sulfur-based antioxidants, and phosphine-based antioxidants, but are not limited thereto.

Specific examples of the antioxidant may include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate and triethyl phosphate, hindered phenol-based primary antioxidants such as 2, 6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3, 5-di-t-butylphenyl) propionate, tetrakis [ 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-hydroxybenzyl) benzene, 3, 5-di-t-butyl-4-hydroxybenzylphosphine diethyl ester, 2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4 '-butylidene-bis (3-methyl-6-butylphenol), 4' -thiobis (3-methyl-6-t-butylphenol), and bis [3, 3-bis- (4 '-hydroxy-3' -t-butylphenyl) butanoic acid ] ethylene glycol ester, amine-based antioxidants such as triphenylamine-24-triphenylamine-p-butylphenyl-naphthylamine, N '-benzylthiophenylphosphine-bis (3, 4' -dodecylphenyl) propionate, N-diphenylmethanedi-octylene-4, N-dodecylbenzenediamine, N '-thiodiphenyl-bis (3-4-octylene) propane, N' -thiodiphenyl-bis (3-4-phenyl) propane, N '-diphenyl-bis (3-butyl-phenyl) propane, N' -thiopropane, N '-diphenyl-bis (3-butyl-diphenyl) propane, N' -thiopropane, N '-diphenyl-bis (3-diphenyl) propane, N' -thiopropane, N '-diphenyl) propane, N' -diphenyl-bis (3.

In addition, the photosensitive resin composition may further include one or more additives selected from the group consisting of: photo-crosslinking sensitizer, curing accelerator, adhesion promoter, surfactant, thermal polymerization inhibitor, ultraviolet absorber, dispersant and leveling agent. The content of the additive is 0.1 to 20% by weight based on the total weight of the solids in the photosensitive resin composition.

As the photo-crosslinking sensitizer, at least one selected from the following may be used: benzophenone-based compounds such as benzophenone, 4, 4-bis (dimethylamino) benzophenone, 4, 4-bis (diethylamino) benzophenone, 2,4, 6-trimethylaminobenzophenone, methylphthalylbenzoate, 3-dimethyl-4-methoxybenzophenone and 3,3,4, 4-tetrakis (t-butylperoxycarbonyl) benzophenone; fluorenone-based compounds such as 9-fluorenone, 2-chloro-9-fluorenone, and 2-methyl-9-fluorenone; thioxanthone-based compounds such as thioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; xanthone-based compounds such as xanthone and 2-methyl xanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone and 2, 6-dichloro-9, 10-anthraquinone; acridine-based compounds such as 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 5-bis (9-acridinylpentane), and 1, 3-bis (9-acridinyl) propane; dicarbonyl compounds such as benzyl, 1,7, 7-trimethyl-bicyclo [2,2,1] heptane-2, 3-dione and 9, 10-phenanthrenequinone; phosphine oxide-based compounds such as 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide; benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, and 2-n-butoxyethyl-4- (dimethylamino) benzoate; amino synergists, such as 2, 5-bis (4-diethylaminobenzylidene) cyclopentanone, 2, 6-bis (4-diethylaminobenzylidene) cyclohexanone and 2, 6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone; coumarin-based compounds such as 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, and 10, 10-carbonylbis [1,1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H,11H-C1] -benzopyranone [6,7,8-ij ] -quinolizin-11-one; chalcone compounds, such as 4-diethylaminochalcone and 4-azidobenzaldehyde acetophenone, 2-benzoylmethylene and 3-methyl-b-naphthalenethiol.

The curing accelerator is used to enhance curing and mechanical strength, and at least one selected from the group consisting of: 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenz

Oxazole, 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).

As the adhesion promoter used in the present invention, at least one selected from the following may be used: methacryloylsilane coupling agents such as methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxysilane, and methacryloxypropyldimethoxysilane, and as the alkyltrimethoxysilane, at least one selected from the group consisting of: octyltrimethoxysilane, dodecyltrimethoxysilane and octadecyltrimethoxysilane.

The surfactant includes a silicon-based surfactant and a fluorine-based surfactant. Specifically, silicon-based surfactants include 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., available from BYK-Chemie GmbH, while fluorine-based surfactants include F-114, F-177, F-410, F-411, F-450, F-390, available from DIC (Dai Nippon Ink & s), and the like, 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-1025, TF-1117SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, 1027SF, TF-1441, TF-1442 and the like, but are not limited thereto.

As the ultraviolet absorber, 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but not limited thereto, and those generally used in the art can be used without limitation.

Examples of the thermal polymerization inhibitor may include at least one selected from the group consisting of: p-phenylmether, hydroquinone, pyrocatechol (pyrocatechol), t-butylcatechol (t-butyl catechol), N-nitrosophenyl hydroxylammonium salt, N-nitrosophenyl hydroxylammonium aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4-thiobis (3-methyl-6-t-butylphenol), 2-methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, but are not limited thereto, and those generally used in the art may be used without limitation.

The dispersant may be used by a method of internally adding the dispersant to the pigment in a form in which the pigment is surface-treated in advance or a method of externally adding the dispersant to the pigment. As the dispersant, a compound type of a nonionic dispersant, an anionic dispersant or a cationic dispersant may be used, and examples thereof include fluorine-based, ester-based, cationic, anionic, nonionic and amphoteric surfactants. These may be used alone or in a combination of two or more.

Specifically, the dispersant may be at least one selected from the group consisting of: polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, ester sulfonates, carboxylic esters, carboxylic salts, alkylamide alkylene oxide adducts, and alkylamines, but are not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamidoamine, and amine-epoxide reaction product, and specific examples of the non-polymeric leveling agent include sulfur-containing non-polymer compounds and nitrogen-containing non-polymer compounds, but are not limited thereto, and those generally used in the art may be used without limitation.

The photosensitive resin composition can be used for manufacturing pigment dispersion type photosensitive materials for color filters of thin film transistor liquid crystal displays (TFT LCDs); a photosensitive material for forming a black matrix of a thin film transistor-liquid crystal display (LCD-TFT) or an organic light emitting diode; a photosensitive material for forming a capping layer; a pillar spacer photosensitive material; photosensitive materials for photocurable coatings, photocurable inks, photocurable adhesives, printing plates, and printed circuit boards; photosensitive materials for Plasma Display Panels (PDP); etc., but the purpose thereof is not particularly limited.

Meanwhile, according to another embodiment of the present invention, a photosensitive material manufactured by using the photosensitive resin composition of the other embodiment may be provided.

Details of the photosensitive resin composition include those described above with respect to other embodiments.

Specifically, the photosensitive material in the form of a film or a pattern may be formed by coating the photosensitive resin composition of the embodiment on a substrate. The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, and the like may be used, and generally a spin coating method is widely used. Further, after the coating film is formed, a part of the residual solvent may be removed under reduced pressure, if necessary.

As a light source for curing the photosensitive resin composition, for example, a mercury vapor arc, a carbon arc, a Xe arc, or the like that emits light having a wavelength of 250nm to 450nm can be mentioned, but is not necessarily limited thereto.

Meanwhile, according to another embodiment of the present invention, a color filter including the photosensitive material of the embodiment may be provided.

Details of the photosensitive material include those described above with respect to other embodiments.

A color filter may be manufactured by using a photosensitive resin composition including the compound of one embodiment. The color filter may be formed by: the photosensitive resin composition is coated on a substrate to form a coating film, and then the coating film is exposed, developed, and cured.

The photosensitive resin composition is excellent in heat resistance and less in color change due to heat treatment, and thus can provide a color filter having high color reproducibility as well as high brightness and contrast even during curing in the manufacture of a color filter.

The substrate may be a glass plate, a silicon wafer, or a plastic substrate (e.g., Polyethersulfone (PES), Polycarbonate (PC)), or the like, and the kind thereof is not particularly limited.

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

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

For the purpose of improving contrast, a lattice-shaped black pattern called a black matrix may be arranged between color pixels of the color filter. Chromium may be used as a material of the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process may be used. However, in consideration of high cost of process, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix according to a pigment dispersion method capable of microfabrication may be used.

The formation of the black matrix according to an embodiment of the present invention may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having weak light-shielding properties is added, the strength of the film or the adhesion to the substrate is not lowered even if the amount of the color material is relatively increased.

Meanwhile, according to another embodiment of the present invention, a display device including the color filter of the above embodiment may be provided.

Details of the color filters include those described above with respect to other embodiments.

The display device may be any one of a Plasma Display Panel (PDP), a Light Emitting Diode (LED) display, an Organic Light Emitting Diode (OLED) display, a Liquid Crystal Display (LCD), a thin film transistor-liquid crystal display (TFT-LCD), and a Cathode Ray Tube (CRT).

Advantageous effects

According to the present invention, a compound having excellent color characteristics, heat resistance and solvent resistance can be provided; a photosensitive resin composition using the same; and a photosensitive material, a color filter and a display device manufactured by using the same.

Detailed Description

Embodiments of the present invention will now be described in more detail by the following examples. However, these examples are provided for illustrative purposes only and are not intended to limit the scope of the present disclosure.

< preparation examples 1 and 2>

Preparation example 1

Compound a-1 was synthesized by the reaction shown in reaction scheme 1 below.

[ reaction scheme 1]

25g (157.041mmol, 1 equivalent) of Compound 1 was added to 200g of dichloromethane (MC, manufacturer: DAEJUNG) and stirred. An ice bath was provided and the reaction solution was brought to 0 ℃. 19.07g (188.454mmol, 1.2 equiv.) of Triethylamine (TEA) were slowly added dropwise to the reaction solution.

Then, 30.787g (174.321mmol, 1.11 equivalents) of compound 2 was slowly added dropwise to the reaction solution. The mixture was allowed to react at 0 ℃ for 30 minutes and then stirred at room temperature for 24 hours. To the reaction solution was added 300g of distilled water (DI water) and stirred for 30 minutes, and the organic layer and the aqueous layer were separated. To the separated aqueous layer was added 200ml of MC and further extracted. To the organic layer was added 200ml of 5% K₂CO₃The solution was stirred and then the organic layer was separated. Extraction was repeated until distilled water was added to the organic layer and the solution was neutralized. The organic layer was subjected to reduced pressure and the solvent was removed. The precipitate was added to 500ml of Ethyl Acetate (EA) in a 1: 3 ratio: a solution of n-hexane was stirred and filtered under reduced pressure. The precipitate was dried at 80 ℃ for one day to obtain 45.736g (152.79mmol) of Compound A-1 as a white solid (yield: 97%).

1H NMR(500MHz，CDCl₃)：8.00～7.97(t，3H)，7.70～7.68(d，1H)，7.66～7.65(d，1H)，7.59～7.55(t，1H)，7.47～7.42(q，3H)，7.21～7.20(d，1H)，2.51(s，3H)

Preparation example 2

Compound A-2 was synthesized in the same manner as in preparation example 1, except that 39.339g (174.321mmol, 1.11 equivalents) of Compound 3 was used in place of Compound 2, as shown in the following reaction scheme 2.

[ reaction scheme 2]

< examples 1 to 12: production of Compound, photosensitive resin composition and photosensitive Material >

Example 1

(1) Preparation of the Compounds

Compound C-1 was synthesized by the reaction shown in reaction scheme 3 below.

[ reaction scheme 3]

In a two-necked round-bottomed flask were added 1g (3.399mmol) of A-1, 0.518g (1.670mmol) of B-1, 1g of benzoic acid and 10ml of methyl benzoate and stirred at 180 ℃ for 5 hours. Then, 100ml of methanol was added, and the precipitated substance was filtered under reduced pressure and then dried in an oven. Thus, 1.05g (1.2024mmol) of Compound C-1 was obtained (yield: 72%).

The results of MS measurement of Compound C-1 are shown below.

Ionization mode ═: APCI +: 873[ M + H ] +, accurate mass: 872

(2) Preparation of photosensitive resin composition

5.554g of the above-synthesized compound C-1, 10.376g of a binder resin [ a copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70: 30, acid value 113KOH mg/g, weight average molecular weight measured by GPC 20000g/mol, molecular weight distribution (PDI) of 2.0, solid content (s.c)) of 25%, and containing a solvent (PGMEA) ], 2.018g of a photoinitiator (I-369, BASF), 1.016g of an additive (F-475, cordic.), 12.443g of a photopolymerizable compound (dipentaerythritol hexaacrylate (DPHA), manufactured by Nippon Kayaku co., ltd.) and 68.593g of a solvent (propylene glycol monomethyl ether acetate, PGMEA) were mixed to manufacture a photosensitive resin composition.

(3) Preparation of photosensitive materials

The photosensitive resin composition was spin-coated on glass (5cm X5 cm) and pre-baked at 100 ℃ for 100 seconds to form a film. The distance between the substrate having the film formed thereon and the photomask was set to 250 μm, and an exposure machine was used at 40mJ/cm²The exposure dose of (a) irradiates the front surface of the substrate. Thereafter, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post-baked at 230 ℃ for 20 minutes to manufacture a substrate.

Example 2

(1) Preparation of the Compounds

0.9g (1.051mmol) of Compound C-2 was synthesized in the same manner as in example 1 except that 0.493g (1.590mmol) of B-2 was used in place of Compound B-1, as shown in the following reaction scheme 4 (yield: 66%).

The results of MS measurement of Compound C-2 are as follows.

Ionization mode ═: APCI +: m/z 857[ M + H ] +, exact mass: 856

[ reaction scheme 4]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-2 was used in place of the compound C-1.

Example 3

(1) Preparation of the Compounds

1.1g (1.284mmol) of Compound C-3 was synthesized in the same manner as in example 1 except that 0.493g (1.590mmol) of B-3 was used in place of Compound B-1 as shown in the following reaction scheme 5 (yield: 81%).

The results of MS measurement of Compound C-3 are as follows.

Ionization mode ═: APCI +: m/z 857[ M + H ] +, exact mass: 856

[ reaction scheme 5]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-3 was used in place of the compound C-1.

Example 4

(1) Preparation of the Compounds

1.26g (1.343mmol) of Compound C-4 was synthesized in the same manner as in example 1 except that 0.512g (1.590mmol) of B-4 was used in place of Compound B-1 as shown in the following reaction scheme 6 (yield: 85%).

The results of MS measurement of Compound C-4 are as follows.

Ionization mode ═: APCI +: 884[ M + H ] +, accurate mass: 885

[ reaction scheme 6]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-4 was used in place of the compound C-1.

Example 5

(1) Preparation of the Compounds

0.82g (0.843mmol) of Compound C-5 was synthesized in the same manner as in example 1 except that 0.652g (1.590mmol) of B-5 was used in place of Compound B-1, as shown in the following reaction scheme 7 (yield: 53%).

The results of MS measurement of Compound C-5 are as follows.

Ionization mode ═: APCI +: 949[ M + H ] +, accurate mass: 948

[ reaction scheme 7]

(2) Photosensitive resin composition and production of photosensitive material

A photosensitive resin composition and a photosensitive material were produced in the same manner as in example 1, except that the compound C-5 was used in place of the compound C-1.

Example 6

(1) Preparation of the Compounds

1.3g (1.288mmol) of Compound C-6 was synthesized in the same manner as in example 1 except that 0.706g (1.590mmol) of B-6 was used in place of Compound B-1 as shown in the following reaction scheme 8 (yield: 81%).

The results of MS measurement of Compound C-6 are as follows.

Ionization mode ═: APCI +: 949[ M + H ] +, accurate mass: 948

[ reaction scheme 8]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-6 was used in place of the compound C-1.

Example 7

(1) Preparation of the Compounds

1g (1.030mmol) of Compound C-7 was synthesized in the same manner as in example 1 except that 1g (2.262mmol) of A-2 was used in place of Compound A-1, and 0.444g (1.431mmol) of B-1 was used, as shown in the following reaction scheme 9 (yield: 71.9%).

The results of MS measurement of Compound C-7 are as follows.

Ionization mode ═: APCI +: m/z 973[ M + H ] +, exact mass: 972

[ reaction scheme 9]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-7 was used in place of the compound C-1.

Example 8

(1) Preparation of the Compounds

0.9g (0.941mmol) of Compound C-8 was synthesized in the same manner as in example 1 except that 1g (2.862mmol) of A-2 was used in place of Compound A-1, and 0.421g (1.431mmol) of B-2 was used, as shown in the following reaction scheme 10 (yield: 65.8%).

The results of MS measurement of Compound C-8 are as follows.

Ionization mode ═: APCI +: m/z 957[ M + H ] +, exact mass: 956

[ reaction scheme 10]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-8 was used in place of the compound C-1.

Example 9

(1) Preparation of the Compounds

0.9g (0.941mmol) of compound C-9 was synthesized in the same manner as in example 1 except that 1g (2.862mmol) of A-2 was used in place of compound A-1 and 0.421g (1.431mmol) of B-3 was used, as shown in the following reaction scheme 11 (yield: 65.8%).

The results of MS measurement of Compound C-9 are as follows.

Ionization mode ═: APCI +: m/z 957[ M + H ] +, exact mass: 956

[ reaction scheme 11]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-9 was used in place of the compound C-1.

Example 10

(1) Preparation of the Compounds

1g (1.015mmol) of Compound C-10 was synthesized in the same manner as in example 1 except that 1g (2.862mmol) of A-2 was used in place of Compound A-1, and 0.461g (1.431mmol) of B-4 was used, as shown in the following reaction scheme 12 (yield: 71%).

The results of MS measurement of Compound C-10 are as follows.

Ionization mode ═: APCI +: m/z 985[ M + H ] +, exact mass: 984

[ reaction scheme 12]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-10 was used in place of the compound C-1.

Example 11

(1) Preparation of the Compounds

0.78g (0.730mmol) of Compound C-11 was synthesized in the same manner as in example 1 except that 1g (2.862mmol) of A-2 was used in place of Compound A-1, and 0.586g (1.431mmol) of B-5 was used, as shown in the following reaction scheme 13 (yield: 51%).

The results of MS measurement of Compound C-11 are as follows.

Ionization mode ═: APCI +: 1073[ M + H ] +, exact mass: 1072

[ reaction scheme 13]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-11 was used in place of the compound C-1.

Example 12

(1) Preparation of the Compounds

1.16g (1.045mmol) of compound C-12 was synthesized in the same manner as in example 1 except that 1g (2.862mmol) of A-2 was used in place of compound A-1 and 0.636g (1.431mmol) of B-6 was used, as shown in the following reaction scheme 14 (yield: 73%).

The results of MS measurement of Compound C-12 are as follows.

Ionization mode ═: APCI +: 1107[ M + H ] +, exact mass: 1106

[ reaction scheme 14]

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that the compound C-12 was used in place of the compound C-1.

< comparative example: production of Compound, photosensitive resin composition and photosensitive Material >

Comparative example 1

(1) Preparation of the Compounds

PY138 pigment having the following chemical structure was used.

(2) Photosensitive resin composition and preparation of photosensitive material

A photosensitive resin composition and a photosensitive material were prepared in the same manner as in example 1, except that PY138 was used instead of the compound C-1.

< experimental examples: measurement of physical Properties of Compound, photosensitive resin composition, and photosensitive Material >

Physical properties of the photosensitive resin compositions or photosensitive materials obtained in examples and comparative examples were measured by the following methods, and the results are shown in tables 1 to 3 below.

1. Solvent resistance

The solubility of each compound obtained in examples and comparative examples in Dimethylformamide (DMF) as an organic solvent was measured, the solvent resistance was evaluated according to the following criteria, and the results are shown in table 1 below.

○ solubility of 1% or more

X: the solubility is less than 1 percent

[ TABLE 1]

Results of Experimental example 1

As shown in table 1, the compounds of the examples have improved solubility in organic solvents compared to the comparative examples. The increase in solubility appears to be due to the SO contained in the compounds of the examples₃A functional group.

Therefore, unlike general pigments which need to be dispersed by a derivative, a dispersant, or the like when dissolved in an organic solvent, the compounds of the examples do not need a derivative or a dispersant when dissolved in an organic solvent, and thus can be easily commercially applied.

2. Evaluation of Heat resistance

The transmission spectrum of the prebaked substrate obtained in the example in the visible light region in the range of 380nm to 780nm was obtained by using a spectroscope (MCPD-OTSUKA).

The pre-baked substrate was then post-baked at 230 ℃ for a further 20 minutes to obtain a transmission spectrum for the same equipment and measurement range.

The calculation of Eab was performed by using the obtained transmission spectrum and the values E (L, a, b) obtained using a C light source backlight, and the results are shown in table 2 below.

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

Eab ═ Δ E (L, a, b) } after post bake [ (. L, a, b) } Δ E (L, a, b) }after pre bake

A small value of Eab means excellent color heat resistance. In the case of a material related to a color filter, when the Eab value is less than 3, it is considered to be an excellent material.

[ TABLE 2]

Results of Experimental example 2

As shown in table 2, the photosensitive material of the example had a small Eab value of less than 3, indicating that it exhibited excellent color heat resistance.

Claims (11)

1. A compound represented by the following chemical formula 1-1:

[ chemical formula 1-1]

Wherein, in chemical formula 1-1,

a is a direct bond, an ether group, a carbonyl group, a diester group or-C (CF)₃)₂-, and

r27 and R28 are the same as or different from each other, and each is independently phenyl or naphthyl.

2. The compound of claim 1, wherein the diester group comprises a functional group represented by the following chemical formula 2:

[ chemical formula 2]

Wherein, in chemical formula 2, X is an alkylene group having 1 to 10 carbon atoms, a heteroalkylene group having 1 to 10 carbon atoms, a haloalkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.

3. The compound according to claim 1, wherein the compound of chemical formula 1-1 is represented by the following chemical formula 1-2 or 1-3:

[ chemical formulas 1-2]

[ chemical formulas 1-3]

Wherein, in chemical formula 1-2 or 1-3,

a is a direct bond, an ether group, a carbonyl group, a diester group or-C (CF)₃)₂-, and

r28 to R31 are the same as or different from each other, and are each independently phenyl or naphthyl.

4. The compound according to claim 1, wherein the compound of chemical formula 1-1 is represented by any one of the following chemical formulae 1-4 to 1-15:

[ chemical formulas 1 to 4]

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

[ chemical formulas 1 to 7]

[ chemical formulas 1 to 8]

[ chemical formulas 1 to 9]

[ chemical formulas 1-10]

[ chemical formulas 1 to 11]

[ chemical formulas 1 to 12]

[ chemical formulas 1 to 13]

[ chemical formulas 1 to 14]

[ chemical formulas 1 to 15]

5. A color material composition comprising the compound of claim 1.

6. The color material composition of claim 5, further comprising at least one of a dye and a pigment.

7. A photosensitive resin composition comprising the compound according to claim 1 or the color material composition according to claim 5; a binder resin; a polyfunctional monomer; a photoinitiator and a solvent.

8. The photosensitive resin composition according to claim 7, wherein the compound is contained in an amount of 5 to 60 wt% based on the total weight of solids in the photosensitive resin composition.

9. A photosensitive material comprising the photosensitive resin composition according to claim 7.

10. A color filter comprising the photosensitive material according to claim 9.

11. A display device comprising the color filter according to claim 10.