KR20200137750A - Compound, photosensitive resin composition comprising same, photosensitive material, color filter and display device - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, with excellent heat resistance, to a photosensitive resin composition comprising the same, to a photosensitive material, to a color filter, and to a display device.

Description

Compound, photosensitive resin composition containing the same, photosensitive material, color filter, display device {COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION COMPRISING SAME, PHOTOSENSITIVE MATERIAL, COLOR FILTER AND DISPLAY DEVICE}

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

Recently, a color filter is required to have high luminance and high contrast ratio. In addition, one of the main objectives of the development of a display device is to differentiate display device performance through improved color purity and to improve productivity in a manufacturing process.

Conventionally, since the pigment type used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, they are aggregated in a color filter, so that dissolution and dispersibility are inferior, and multiple scattering of light occurs due to large aggregated particles. The scattering of polarized light has been pointed out as the main factor that lowers the contrast ratio. Efforts have been made to improve brightness and contrast ratio through ultra-fine pigmentation and dispersion stabilization, but the degree of freedom is limited in selecting a color material for realizing color coordinates for high-color purity display devices. In addition, the already developed color material, particularly the pigment dispersion method using a pigment, has reached its limit in improving the color purity, brightness, and contrast ratio of a color filter using the same.

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

Korean Patent Publication No. 2001-0009058

The present specification is to provide a compound, a photosensitive resin composition comprising the same, a photosensitive material manufactured using the same, a color filter, and a display device.

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

[Formula 1]

In Formula 1,

M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr,

When M is Al, M is combined with -O(P=O)R'R'',

R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group,

R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,

At least one of R1 to R16 is a halogen group, and at least one of the substituents other than a halogen group of R1 to R16 is -OR,

R is a substituted or unsubstituted heterocyclic group.

An exemplary embodiment of the present specification, the compound represented by Formula 1; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.

An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition.

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

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

The compound according to an exemplary embodiment of the present specification may be used as a colorant in the photosensitive resin composition, and has solubility in an organic solvent, so that the dispersion process can be reduced. When applying a conventional pigment, unlike the dispersion process, The compound can be used as a colorant in an economical way.

In addition, the compound according to an exemplary embodiment of the present specification is excellent in heat resistance.

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

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

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

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

[Formula 1]

In Formula 1,

M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr,

When M is Al, M is combined with -O(P=O)R'R'',

R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group,

R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,

At least one of R1 to R16 is a halogen group, and at least one of the substituents other than a halogen group of R1 to R16 is -OR,

R is a substituted or unsubstituted heterocyclic group.

The present invention has excellent solubility in an organic solvent by including the compound represented by Formula 1 above. Specifically, the solubility of the compound may be increased by including a substituent of O substituted with at least one heterocyclic group in the phthalocyanine structure.

In addition, in Formula 1, the substituent of O substituted with at least one heterocyclic group serves as an electron donating, and at least one halogen group serves as an electron withdrawing, so that the electron balance ), the heat resistance can be increased.

Due to the increase in solubility, it is possible to prevent aggregation between color materials, and through this, it is possible to increase economic efficiency by reducing the amount of material required for dispersing color materials. In addition, it is possible to improve the contrast ratio (CR) and have excellent heat resistance.

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

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

Means a site bonded to another substituent or a bonding portion.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Aryl group; Heteroaryl group; Acryloyl group; Acrylate group; It means that it is substituted with one or more substituents selected from the group containing a heterocyclic group and an anionic group including one or more of N, O, S, or P atoms, or does not have any substituents.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the ring means an aromatic or aliphatic ring in that adjacent groups can be bonded to form a “ring”. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. The aryl group and the heteroaryl group may be described below.

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

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

In the present specification, the number of carbon atoms of the aryloxy group is not particularly limited, but may be 6 to 30, specifically 6 to 20, and more specifically 6 to 12. The'aryl' of the aryloxy group may be an aryl group to be described later, or a heteroaryl group.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms 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 include 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-oxy And the like, but are not limited to these.

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

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkenyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group are preferably an alkenyl group substituted with an aryl group such as a stylbenyl group and a styrenyl group, but are not limited thereto.

In the present specification, the cycloalkenyl group is not particularly limited, but is preferably 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group are preferably a cyclopentenylene group and a cyclohexenylene group, but are 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 an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbons is not particularly limited, but has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl group, pyridazine group , Quinolinyl group, isoquinolinyl group, indole group, carbazolyl group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophenyl group, benzothianopyridinyl group, dibenzothiophenyl group, Benzofuropyridinyl group, benzofuranyl group, dibenzofuranyl group, 2-methylisoindoline-1,3-dioyl group, 2-phenylisoindoline-1,3-dioyl group, etc., but these It is not limited to

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

In the present specification, the acryloyl group refers to a photopolymerizable unsaturated group, for example, a (meth)acryloyl group, but is not limited thereto.

In the present specification, the acrylate group refers to a photopolymerizable unsaturated group, such as a (meth)acrylate group, but is 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 of'(meth)acrylate' has the same meaning.

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

In the present specification, the heteroalkylene group means that there are two bonding positions in an alkane containing O, N or S as a hetero atom. The heteroalkylene group may be straight chain, branched chain or cyclic chain. The number of carbon atoms of the heteroalkylene group is not particularly limited, but, for example, 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

In an exemplary embodiment of the present specification, M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr.

In an exemplary embodiment of the present specification, M is Cu; Zn; Or Al.

In an exemplary embodiment of the present specification, M is Cu.

In an exemplary embodiment of the present specification, M is Zn.

In an exemplary embodiment of the present specification, M is Al.

In the exemplary embodiment of the present specification, when M is Al, M is combined with -O(P=O)R'R''.

In the exemplary embodiment of the present specification, R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group.

In the exemplary embodiment of the present specification, R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryloxy group having 6 to 12 carbon atoms.

In the exemplary embodiment of the present specification, R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group.

In the exemplary embodiment of the present specification, R'and R'' are the same as or different from each other, and each independently a phenyl group.

In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR.

In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; Halogen group; Or -OR.

In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; Goat; bromine; Or -OR.

In an exemplary embodiment of the present specification, R3, R7, R11 and R15 are -OR.

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

In an exemplary embodiment of the present specification, R1, R2, R4 to R6, R8 to R10, R12 to R14 and R16 are chlorine; Or bromine.

In an exemplary embodiment of the present specification, R13, R14, and R16 are chlorine; Or bromine.

In an exemplary embodiment of the present specification, R1 to R12 are hydrogen.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted quinolinyl group; A substituted or unsubstituted isoquinolinyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; A substituted or unsubstituted benzofuropyridinyl group; A substituted or unsubstituted benzothianopyridinyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted 2-methylisoindoline-1,3-dioyl group; Or a substituted or unsubstituted 2-phenylisoindolin-1,3-dioyl group.

In the exemplary embodiment of the present specification, R is a quinolinyl group; Isoquinolinyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Benzofuropyridinyl group; Benzothianopyridinyl group; A carbazolyl group unsubstituted or substituted with a methyl group, a 2-ethylhexyl group, or a phenyl group; 2-methylisoindoline-1,3-dioyl group; Or a 2-phenylisoindolin-1,3-dioyl group.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 2.

[Formula 2]

In Formula 2,

M is the same as the definition in Formula 1,

R1 to R14 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,

At least one of R1 to R14 and R16 is a halogen group,

R and Z1 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, the definition of Z1 is the same as the definition of R described above.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

M is the same as the definition in Formula 1,

R1, R2, R4 to R6, R8 to R10, R12 to R14 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,

At least one of R1, R2, R4 to R6, R8 to R10, R12 to R14 and R16 is a halogen group,

R and Z1 to Z4 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, the definitions of Z1 to Z4 are the same as those of R described above.

In an exemplary embodiment of the present specification, at least one of R1 to R14 and R16 is a halogen group.

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

An exemplary embodiment of the present specification is the compound; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.

The photosensitive resin composition may further include at least one of a dye and a pigment in addition to the compound of Formula 1 above. For example, the color material composition may include only the compound of Formula 1, but includes the compound of Formula 1 and at least one dye, the compound of Formula 1 and at least one pigment, or the compound of Formula 1 , One or more dyes and one or more pigments may be included.

The photosensitive resin composition may further include a pigment dispersion. The pigment dispersion may be, for example, Pigment Yellow 138, 139, 185 pigment dispersion, but is not limited thereto.

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

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

Polyfunctional monomers that impart mechanical strength of the film include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And it may be any one or more of an acid anhydride.

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

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

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

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

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

According to an exemplary 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 to 50,000.

The acid value of the binder resin can be measured by titration with a 0.1N concentration of potassium hydroxide (KOH) methanol solution, and the weight average molecular weight can be measured using gel permeation chromatography (GPC).

The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, and 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 polyfunctional monomer may be specifically dipentaerythritol hexaacrylate (DPHA).

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

The acetophenone compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-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. , Is not limited thereto.

The triazine 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, but are not limited thereto.

The oxime compound is 1,2-octadione-1-(4-phenylthio)phenyl-2-(o-benzoyloxime) (Shibagagi Co., Ltd., Shijii 124), ethanone-1-(9-ethyl) -6-(2-methylbenzoyl-3-yl)-1-(O-acetyloxime)(CGI 242), N-1919 (Adeca), and the like, but are not limited thereto.

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

The solvent is specifically propylene glycol methyl ether acetate (PGMEA).

An exemplary embodiment of the present specification is based on the total weight of the photosensitive resin composition, 5 to 60% by weight of the compound represented by Formula 1, 1 to 60% by weight of the binder resin, 0.1 to 50% by weight of the multifunctional monomer, the It provides a photosensitive resin composition comprising 0.1 to 20% by weight of a photoinitiator and 10 to 80% by weight of the solvent.

The photosensitive resin composition may further include 5 to 20% by weight of a pigment dispersion based on the total weight of the photosensitive resin composition.

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

The total weight of the solid content means the sum of the total weight of 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 a general analysis 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 is 1 or 2 selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant, a dispersant, and a leveling agent. It further contains the above additives.

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

The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Fluorenone compounds such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, 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]heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo Coumarin compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.

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

The adhesion promoter used in this specification is methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents such as may be selected and used, and as an alkyl trimethoxy silane, one or more types of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. You can choose and use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-Chemie's 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, and as a fluorine-based surfactant, DIC (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, and the like may be used, but are not limited thereto.

The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, 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 diethylester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-di- 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 Hindered phenol-based primary antioxidants such as ester); 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 dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane Secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1 ,1'-biphenyl)-4,4'-diylbisphosphonoic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester ((1,1'-Biphenyl)-4,4 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 the present invention is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, 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- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and the technology It may include those generally known in the field.

The dispersant may be used as a method of adding the pigment inside to the pigment in the form of surface treatment in advance, or adding it to the pigment outside. Compound type, nonionic, anionic or cationic dispersants can be used as the dispersant, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants and the like can be used. These may be used individually or in combination of two or more.

Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylate, There may be 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 polymeric leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Including a compound, but is not limited thereto, all those generally used in the art may be used.

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

The photosensitive material including the photosensitive resin composition refers to forming a photosensitive material in the form of a thin film or pattern by applying and curing the photosensitive resin composition of the present specification on a substrate in an appropriate manner.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. Further, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.

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

The resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode, It can be used for overcoat layer formation photosensitive material, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), and limited to its use. Is not specifically placed.

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

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

The resin composition according to the exemplary embodiment of the present specification has excellent heat resistance, and has little change in color due to heat treatment, so that a color filter having high color reproducibility and high luminance and contrast ratio can be provided even by a curing process when manufacturing a color filter. have.

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

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

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

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

The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a colored pigment may be used.At this time, since a colored pigment having insufficient light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material increases. There is an advantage that does not work.

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

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

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

<Example>

Compound synthesis

Synthesis Example 1: 3,4,6-trichloro-5-(quinolin-8-yloxy)phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5g, 18.804mmol) and quinolin-8-ol (2.23g, 18.804mmol) were added to 50 ml of dimethyl sulfoxide (DMSO) and stirred at room temperature. After that, lithium hydroxide momohydrate (0.789g, 18.804mmol) was slowly added to the reaction solution. Thereafter, the mixture was stirred at room temperature for 24 hours, and the mixture was added dropwise to 500ml of H ₂ O. The precipitate was filtered under reduced pressure, and extracted with CHCl ₃ and brine. The organic layer was separated, passed through MgSO _4, and the solvent was removed under reduced pressure. Thereafter, the crude product was separated through column chromatography to obtain a compound of Synthesis Example 1.

[Synthesis Example 1 compound]

Synthesis Example 2: 3,4,6-trichloro-5-(dibenzo[b,d]furan-1-yloxy)phthalonitrile

In Synthesis Example 1, dibenzo[b,d]furan-1-ol was used instead of quinolin-8-ol, and the others were carried out in the same manner to obtain a compound of Synthesis Example 2.

[Synthesis Example 2 compound]

Synthesis Example 3: 3,4,6-trichloro-5-(dibenzo[b,d]thiophen-1-yloxy)phthalonitrile

Dibenzo[b,d]thiophen-1-ol was used instead of quinolin-8-ol in Synthesis Example 1, and the others were carried out in the same manner to obtain a compound of Synthesis Example 3.

[Synthesis Example 3 compound]

Synthesis Example 4: 4-((9H-carbazol-4-yl)oxy)-3,5,6-trichlorophthalonitrile

In Synthesis Example 1, 9H-carbazol-4-ol was used instead of quinolin-8-ol, and the others were carried out in the same manner to obtain a compound of Synthesis Example 4.

[Synthesis Example 4 compound]

Synthesis Example 5: 3,4,6-trichloro-5-((9-(2-ethylhexyl)-9H-carbazol-4-yl)oxy)phthalonitrile

In Synthesis Example 1, 9-(2-ethylhexyl)-9H-carbazol-4-ol was used instead of quinolin-8-ol, and the others were carried out in the same manner to obtain a compound of Synthesis Example 5.

[Synthesis Example 5 compound]

Synthesis Example 6: 3,4,6-tribromo-5-(quinolin-8-yloxy)phthalonitrile

In Synthesis Example 1, 3,4,5,6-tetrabromophthalonitrile was used instead of 3,4,5,6-tetrachlorophthalonitrile, and the others were carried out in the same manner to obtain a compound of Synthesis Example 6.

[Synthesis Example 6 compound]

Synthesis Example 7: 3,4,6-tribromo-5-(dibenzo[b,d]furan-1-yloxy)phthalonitrile

In Synthesis Example 2, 3,4,5,6-tetrabromophthalonitrile was used instead of 3,4,5,6-tetrachlorophthalonitrile, and the others were carried out in the same manner to obtain a compound of Synthesis Example 7.

[Synthesis Example 7 compound]

Synthesis Example 8: 3,4-dibromo-6-chloro-5-(dibenzo[b,d]thiophen-1-yloxy)phthalonitrile

In Synthesis Example 3, 3,4,5,6-tetrabromophthalonitrile was used instead of 3,4,5,6-tetrachlorophthalonitrile, and the others were carried out in the same manner to obtain a compound of Synthesis Example 8.

[Synthesis Example 8 compound]

Synthesis Example 9: 4-((9H-carbazol-4-yl)oxy)-3,5,6-tribromophthalonitrile

In Synthesis Example 4, 3,4,5,6-tetrabromophthalonitrile was used instead of 3,4,5,6-tetrachlorophthalonitrile, and the others were carried out in the same manner to obtain a compound of Synthesis Example 9.

[Synthesis Example 9 compound]

Synthesis Example 10: 3,4,6-tribromo-5-((9-(2-ethylhexyl)-9H-carbazol-4-yl)oxy)phthalonitrile

In Synthesis Example 5, 3,4,5,6-tetrabromophthalonitrile was used instead of 3,4,5,6-tetrachlorophthalonitrile, and the others were carried out in the same manner to obtain a compound of Synthesis Example 10.

[Synthesis Example 10 compound]

Synthesis Example 11: Synthesis of Compound 11

Synthesis Example 1 Compound 3.389g (9.047mmol), ZnCl ₂ 0.37g (2.714mmol) was added to 1-pentanol 50ml, the temperature was raised to 90 ℃ and stirred for 30 minutes. Thereafter, 1.377 g (9.047 mmol) of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) was slowly added dropwise. Thereafter, the reaction mixture was heated to 135° C. and reacted for 24 hours. The reaction was cooled to room temperature, and slowly added dropwise to a mixed solution prepared with 240 ml of MeOH and 480 ml of H ₂ O. The precipitate was filtered under reduced pressure, and washed with a mixed solution prepared with 120 ml of MeOH and 240 ml of H ₂ O. This was separated through column chromatography to obtain Compound 11 prepared in Synthesis Example 11.

[Compound 11] MALDI-TOF MS: 1563.80 m/z

Synthesis Example 12: Synthesis of Compound 12

In Synthesis Example 11, the compound of Synthesis Example 2 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 12 prepared by Synthesis Example 12.

[Compound 12] MALDI-TOF MS: 1719.93 m/z

Synthesis Example 13: Synthesis of Compound 13

In Synthesis Example 11, the compound of Synthesis Example 3 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 13 prepared by Synthesis Example 13.

[Compound 13] MALDI-TOF MS: 1784.18 m/z

Synthesis Example 14: Synthesis of Compound 14

In Synthesis Example 11, the compound of Synthesis Example 4 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 14 prepared by Synthesis Example 14.

[Compound 14] MALDI-TOF MS: 1716.00 m/z

Synthesis Example 15: Synthesis of Compound 15

In Synthesis Example 11, the compound of Synthesis Example 5 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 15 prepared by Synthesis Example 15.

[Compound 15] MALDI-TOF MS: 2164.86 m/z

Synthesis Example 16: Synthesis of Compound 16

In Synthesis Example 11, the compound of Synthesis Example 6 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 16 prepared by Synthesis Example 16.

[Compound 16] MALDI-TOF MS: 2097.25 m/z

Synthesis Example 17: Synthesis of Compound 17

In Synthesis Example 11, the compound of Synthesis Example 7 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 17 prepared by Synthesis Example 17.

[Compound 17] MALDI-TOF MS: 2253.38 m/z

Synthesis Example 18: Synthesis of Compound 18

In Synthesis Example 11, the compound of Synthesis Example 8 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 18 prepared by Synthesis Example 18.

[Compound 18] MALDI-TOF MS: 2317.62 m/z

Synthesis Example 19: Synthesis of Compound 19

In Synthesis Example 11, the compound of Synthesis Example 9 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 19 prepared by Synthesis Example 19.

[Compound 19] MALDI-TOF MS: 2249.44 m/z

Synthesis Example 20: Synthesis of Compound 20

In Synthesis Example 11, the compound of Synthesis Example 10 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound 20 prepared by Synthesis Example 19.

[Compound 20] MALDI-TOF MS: 2698.31 m/z

Synthesis Examples 21-30: Synthesis of compounds 20-30

In Synthesis Examples 11-20, CuCl _{2 was} used instead of ZnCl ₂ , and the others were carried out in the same manner to obtain compounds 21-30 prepared in Synthesis Examples 21-30

.

.

<Comparative Example>

Comparative Example 1: Synthesis of the compound represented by Comparative Compound 1

In Synthesis Example 11, 4-(quinolin-8-yloxy)phthalonitrile was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain Comparative Compound 1 prepared in Comparative Example 1.

Comparative Example 2: Synthesis of the compound represented by Comparative Compound 2

In Synthesis Example 11, 4-(((9H-carbazol-4-yl)oxy)phthalonitrile was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain Comparative Compound 2 prepared in Comparative Example 2.

Comparative Example 3: Synthesis of the compound represented by Comparative Compound 3

In Synthesis Example 11, 4-((7-(trifluoromethyl)quinolin-4-yl)oxy)phthalonitrile was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain Comparative Compound 3 prepared in Comparative Example 3.

Comparative Example 4: Synthesis of the compound represented by Comparative Compound 4

In Synthesis Example 11, 4-(3,4-dicyanophenoxy)benzoic acid and FeCl _{2 were} used instead of the compound of Synthesis Example 1 and ZnCl ₂ , and the others were carried out in the same manner to obtain Comparative Compound 4 prepared in Comparative Example 4.

Comparative Example 5: Synthesis of the compound represented by Comparative Compound 5

In Synthesis Example 11, instead of the compound of Synthesis Example 1 and ZnCl ₂ , 5-(3,4-dicyanophenoxy)quinoline-8-sulfonic acid and FeCl _{2 were} used, and the others were carried out in the same manner, and Comparative Compound 5 prepared by Comparative Example 5 Got it.

Solubility measurement

To 0.1 g of Synthesis Example Compounds 11 to 30 and Comparative Compounds 1 to 5, propylene glycol methyl ether acetate (PGMEA (Propylene glycol methyl ether acetate)) was added, and the compound solution was shaker (Jeio Tech SK-600). After stirring at 25° C. at 350 rpm for 1 hour, the results of confirming the solubility of the compound are shown in Table 1 below. The solubility evaluation criteria are as follows.

[Solubility evaluation criteria]

Compound (solvent) is dissolved in 5% by weight or more with respect to the total amount of the diluted solvent PGMEA: ○

Dissolution of more than 3% by weight and less than 5% by weight of the compound (solute) based on the total amount of the diluent PGMEA: △

Dissolution of less than 1% by weight of compound (solvent) based on the total amount of diluent PGMEA: Ⅹ

Solubility Compound 11~20 ○ Compounds 21-30 △ Comparative compound 1 ○ Comparative compound 2 ○ Comparative compound 3 △ Comparative compound 4 Ⅹ Comparative compound 5 Ⅹ

From Table 1, Compounds 11 to 30 according to the present specification have better solubility in organic solvents than the compounds of Comparative Compounds 4 to 5, so that an additional dispersion process for using a coloring material and the amount of dispersant used may be reduced. When used, it was confirmed that excellent color characteristics could be displayed.

Preparation of photosensitive resin composition

[Preparation of photosensitive resin composition Example 1]

A photosensitive resin composition according to Example 1 was prepared by mixing with the components shown in Table 2 below.

After dissolving the compound in a solvent (propylene glycol methyl ether acetate), the mixture was stirred for 1 hour with a shaker (Jeio Tech SK-600) at room temperature for 1 hour. Thereafter, a pigment dispersion, a binder resin (alkali-soluble resin), a polyfunctional monomer (photopolymerizable compound), and a photoinitiator were added and further stirred at room temperature for 1 hour. Thereafter, impurities were removed with a 0.2 μm filter to prepare a photosensitive resin composition.

ingredient Content (% by weight) Color material compound Compound 11 5 Pigment dispersion Pigment Yellow 138
Pigment dispersion 15 Binder resin (alkali-soluble resin) 12.5 Polyfunctional monomer (photopolymerizable compound) 6 Photoinitiator 1.5 Solvent (PGMEA) 60 Total amount 100.0 Binder resin (alkali-soluble resin): a copolymer of benzyl methacrylate and methacrylic acid (molar ratio of 70:30, acid value is 113 KOH mg/g, weight average molecular weight measured by gel permeation chromatography (GPC) 20,000 g/mol , Molecular weight distribution (PDI) 2.0, solid content (SC) 25%, including solvent PGMEA
Polyfunctional monomer (photopolymerizable compound): Dipentaerythritol hexaacrylate (DPHA)
Photoinitiator: 2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio)phenyl)propan-1-one (2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio) phenyl)propan-1-one)

[Preparation of photosensitive resin composition Examples 2 to 20]

In the preparation of the photosensitive resin composition Example 1, instead of the compound 11, each of 12 to 30 was used, and other than that, photosensitive resin composition Examples 2 to 20 were prepared by the same method.

[Production of Photosensitive Resin Composition Comparative Examples 1 to 5]

In the preparation of the photosensitive resin composition Example 1, Comparative Compounds 1 to 5 were used instead of Compound 11, respectively, and Comparative Examples 1 to 5 of the photosensitive resin composition were prepared by the same method except for that.

Substrate fabrication, color coordinate, luminance, contrast measurement

The photosensitive resin compositions according to Examples 1 to 20 and Comparative Examples 1 to 5 were each used for preparing a substrate. Specifically, the photosensitive resin composition according to the Examples and Comparative Examples was spin-coated on glass (5 X 5 cm ² ), and prebake was performed at 100° C. for 100 seconds to form a film.

The fabricated substrate was measured for color coordinates (x, y) and luminance (Y) using a spectrometer (MCPD, Otsuka), and are shown in Table 3 below.

compound Color coordinate (x,y) Luminance (Y) Example 1 Compound 11 0.273, 0.577 63.1 Example 2 Compound 12 0.274, 0.576 62.0 Example 3 Compound 13 0.271, 0.571 62.8 Example 4 Compound 14 0.276, 0.577 61.7 Example 5 Compound 15 0.273, 0.580 62.1 Example 6 Compound 16 0.277, 0.581 62.5 Example 7 Compound 17 0.272, 0.579 62.0 Example 8 Compound 18 0.271, 0.586 62.7 Example 9 Compound 19 0.277, 0.571 61.9 Example 10 Compound 20 0.279, 0.582 62.3 Example 11 Compound 21 0.272, 0.577 62.1 Example 12 Compound 22 0.271, 0.580 61.8 Example 13 Compound 23 0.274, 0.571 62.1 Example 14 Compound 24 0.282, 0.581 62.5 Example 15 Compound 25 0.272, 0.584 62.6 Example 16 Compound 26 0.277, 0.578 62.4 Example 17 Compound 27 0.282, 0.571 61.9 Example 18 Compound 28 0.271, 0.584 62.0 Example 19 Compound 29 0.277, 0.587 62.2 Example 20 Compound 30 0.284, 0.580 61.8 Comparative Example 1 Comparative compound 1 0.279, 0.579 61.2 Comparative Example 2 Comparative compound 2 0.273, 0.581 60.1 Comparative Example 3 Comparative compound 3 0.281 0.577 59.3 Comparative Example 4 Comparative compound 4 0.275, 0.571 57.9 Comparative Example 5 Comparative compound 5 0.278, 0.573 58.6

Heat resistance evaluation

A transmittance spectrum of a visible light region in the range of 380 nm to 780 nm was obtained using a spectrometer (MCPD-Otsuka Corporation) prepared according to the substrate manufacturing method. In addition, a prebake substrate was additionally subjected to postbake at 230° C. for 20 minutes to obtain a transmittance spectrum in the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter, ΔEab) was calculated using the obtained values E(L*, a*, b*), and shown in Table 4 below.

Specifically, the equation for calculating ΔEab is as follows.

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

△Eab (post bake-prebake) Examples 1-20 ○ Comparative Example 1 Ⅹ(5.8) Comparative Example 2 Ⅹ(6.1) Comparative Example 3 Ⅹ(5.2) Comparative Example 4 Ⅹ(6.7) Comparative Example 5 Ⅹ(5.5)

[Criteria for evaluating heat resistance]

ΔEab <3 case: ○, ΔEab> 3 case: Ⅹ

According to Tables 3 and 4, it was confirmed that the luminance and heat resistance of the examples were higher than those of the comparative examples. It was confirmed that the compound according to the present specification contained a phthalocyanine structure, so that the contrast ratio was high. Specifically, the compound according to the present specification increases solubility by introducing an aryloxyl group containing a heterocyclic group as a substituent to the phthalocyanine structure, and by introducing an electron withdrawing additionally at least one halogen group, the aryloxyl group Heat resistance can be increased by an electron balance between the electron donor property and the electron withdrawing property of the halogen group.

Claims (11)

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

In Formula 1,
M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr,
When M is Al, M is combined with -O(P=O)R'R'',
R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group,
R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
At least one of R1 to R16 is a halogen group, and at least one of the substituents other than a halogen group of R1 to R16 is -OR,
R is a substituted or unsubstituted heterocyclic group. The method according to claim 1, wherein the formula 1 is a compound represented by the following formula 2:
[Formula 2]

In Formula 2,
M is the same as the definition in Formula 1,
R1 to R14 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
At least one of R1 to R14 and R16 is a halogen group,
R and Z1 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group. The method of claim 1, wherein at least one of R3, R7, R11 and R15 is -OR,
Wherein R is the same as defined in Formula 1 above. The method of claim 1, wherein the formula 1 is a compound represented by the following formula 3:
[Formula 3]

In Chemical Formula 3,
M is the same as the definition in Formula 1,
R1, R2, R4 to R6, R8 to R10, R12 to R14 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
At least one of R1, R2, R4 to R6, R8 to R10, R12 to R14 and R16 is a halogen group,
R and Z1 to Z4 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group. The compound of claim 1, wherein at least one of R1 to R14 and R16 is a halogen group. The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following formulas:

. The compound of any one of claims 1 to 6; Binder resin; Polyfunctional monomers; Photoinitiators; And a photosensitive resin composition containing a solvent. The method according to claim 7, wherein the content of the compound represented by Formula 1 based on the total weight of the solid content in the photosensitive resin composition is 5% by weight to 60% by weight,
The content of the binder resin is 1% to 60% 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. A photosensitive material comprising the photosensitive resin composition according to claim 7. A color filter comprising the photosensitive material according to claim 9. A display device comprising the color filter according to claim 10.