KR20200143927A - 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, to a photosensitive resin composition comprising the same, to a photosensitive material, to a color filter, and to a display device. The compound can be used as a color material in the photosensitive resin composition, and a dispersion process can be reduced.

Description

Compound, photosensitive resin composition containing the same, photosensitive material, color filter, and 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 including 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 including the same, a photosensitive material including 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,

R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or represented by the following formula A,

At least one of R1 to R4, at least one of R5 to R8, at least one of R9 to R12, and at least one of R13 to R16 are represented by the following formula A,

[Formula A]

In the formula A,

는 상기 화학식 1과 연결되는 부분을 의미하고,

Means a moiety connected to Formula 1,

L is a direct bond; A substituted or unsubstituted alkylene group; Or -O-,

l is an integer of 0 to 3, and when l is 2 or more, L is the same as or different from each other,

Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or -OCO-R',

At least one of Ra is a substituted or unsubstituted C3 or less alkyl group; Or in the case of a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group; Or at least one of Ra that is not a substituted or unsubstituted alkoxy group is -OCO-R',

R'is a substituted or unsubstituted aryl group,

ra is an integer of 1 to 4, and when ra is 2 or more, Ra is the same as or different from each other,

Rb is a polymerizable group; Or -COOH, and rb is 0 or 1.

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, when the compound according to the exemplary embodiment of the present specification is used as a coloring material, it is possible to suppress migration, elution, and re-aggregation of dyes, and heat resistance and stability are improved.

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,

R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or represented by the following formula A,

At least one of R1 to R4, at least one of R5 to R8, at least one of R9 to R12, and at least one of R13 to R16 are represented by the following formula A,

[Formula A]

In the formula A,

는 상기 화학식 1과 연결되는 부분을 의미하고,

Means a moiety connected to Formula 1,

L is a direct bond; A substituted or unsubstituted alkylene group; Or -O-,

l is an integer of 0 to 3, and when l is 2 or more, L is the same as or different from each other,

Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or -OCO-R',

At least one of Ra is a substituted or unsubstituted C3 or less alkyl group; Or in the case of a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group; Or at least one of Ra that is not a substituted or unsubstituted alkoxy group is -OCO-R',

R'is a substituted or unsubstituted aryl group,

ra is an integer of 1 to 4, and when ra is 2 or more, Ra is the same as or different from each other,

Rb is a polymerizable group; Or -COOH, and rb is 0 or 1.

The present invention has excellent solubility in an organic solvent by including the compound represented by Formula 1 above. Specifically, when an alkyl or aryloxy group is substituted in the phthalocyanine structure as in the compound according to the present specification, solubility is increased, so that a dispersion process is not required, and an additional material used in the dispersion process is not required.

Due to the increase in solubility, aggregation between color materials can be prevented, and through this, the amount of material required for dispersing the color materials can be reduced, thereby improving economic efficiency.

The compound represented by Formula 1 contains at least one selected from the group consisting of bulky substituents in the core structure, thereby reducing the π-π interaction of phthalocyanine to inhibit re-aggregation between molecules. And heat resistance may be improved.

In addition, by introducing a polymerizable group, chemical resistance can be increased to suppress the possibility of migrating and elution in the process.

As a result, it is possible to inhibit intermolecular aggregation and increase chemical resistance and heat resistance through the present invention.

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; Hydroxy group; -COOH; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Aryl group; Heteroaryl group; Acrylate group; Polymerizable group; It means that it is substituted with one or more substituents selected from the group containing a heterocyclic group containing 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 alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the 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, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, 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, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited to these.

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 polymerizable group means a substituent involved in the polymerization reaction, and is preferably a photopolymerizable group. The polymerizable group refers to a substituent that may be involved in the polymerization reaction by an active radical or acid generated from a photoinitiator described later. The polymerizable group includes, for example, a vinyl group, an epoxy group, an oxetanyl group, or an acrylate 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 the present specification, the alkoxy group may be represented by -ORi, and the description of the aforementioned alkyl group may be applied to Ri.

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 Zn; Or Cu.

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

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

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; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or represented by Formula A.

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; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is represented by the above formula A.

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; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or is represented by Formula A.

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; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or is represented by Formula A.

In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; Or a halogen group, or represented by the above formula A.

In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; Or chlorine, or represented by the above formula A.

In an exemplary embodiment of the present specification, at least one of R1 to R4, at least one of R5 to R8, at least one of R9 to R12, and at least one of R13 to R16 are represented by Formula A.

In an exemplary embodiment of the present specification, at least one of R1 to R4 is represented by Formula A.

In an exemplary embodiment of the present specification, at least one of R5 to R8 is represented by Formula A.

In an exemplary embodiment of the present specification, at least one of R9 to R12 is represented by Formula A.

In an exemplary embodiment of the present specification, at least one of R13 to R16 is represented by Formula A.

In an exemplary embodiment of the present specification, R3, R7, R11, and R15 are represented by Formula A.

In an exemplary embodiment of the present specification, R1, R2, R5, R6, R8, R9, R10, R12 to R14 and R16 are hydrogen; Or goat.

In an exemplary embodiment of the present specification, R1, R2, R5, R6, R8, R9, R10, R12 to R14 and R16 are hydrogen.

In an exemplary embodiment of the present specification, R1, R2, R5, R6, R8, R9, R10, R12 to R14 and R16 are chlorine.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted alkylene group; Or -O-.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; Or -O-.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted C1-C20 alkylene group; Or -O-.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted C 1 to C 10 alkylene group; Or -O-.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted methylene group; A substituted or unsubstituted ethylene group; Or -O-.

In an exemplary embodiment of the present specification, L is a direct bond; Methylene group; Ethylene group; Or -O-.

In the exemplary embodiment of the present specification, l is an integer of 0 to 3.

In an exemplary embodiment of the present specification, l is 0.

In an exemplary embodiment of the present specification, l is 1.

In an exemplary embodiment of the present specification, l is 2.

In an exemplary embodiment of the present specification, l is 3.

In the exemplary embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or -OCO-R'.

In the exemplary embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; 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 -OCO-R'.

In the exemplary embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; 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 -OCO-R'.

In the exemplary embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; 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 -OCO-R'.

In the exemplary embodiment of the present specification, Ra is hydrogen; A substituted or unsubstituted ethyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted phenyl group; Or -OCO-R'.

In the exemplary embodiment of the present specification, Ra is hydrogen; Ethyl group; tert-butyl group; Cyclohexyl group; Methoxy group; Phenyl group; Or -OCO-R'.

In the exemplary embodiment of the present specification, Ra is a substituted or unsubstituted tert-butyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted methoxy group; Or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, at least one of Ra is a substituted or unsubstituted alkyl group having 3 or less carbon atoms; Or in the case of a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group; Or at least one of Ra that is not a substituted or unsubstituted alkoxy group is -OCO-R'.

In "at least one of Ra is a substituted or unsubstituted alkyl group having 3 or less carbon atoms", the "substituted or unsubstituted alkyl group having 3 or less carbon atoms" means a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

In an exemplary embodiment of the present specification, at least one of Ra is a substituted or unsubstituted ethyl group; Or in the case of a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethyl group; Or at least one of Ra that is not a substituted or unsubstituted methoxy group is -OCO-R'. In the exemplary embodiment of the present specification, R'is a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, R'is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R'is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R'is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

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

In the exemplary embodiment of the present specification, Ra is -OCO-R', and R'is a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, Ra is represented by the following formula (B).

[Formula B]

In Formula B,

는 상기 화학식 A과 연결되는 부분을 의미하고,

Means a moiety connected to the formula A,

Rc is hydrogen; heavy hydrogen; Or a substituted or unsubstituted tert-butyl group,

rc is an integer of 2 to 4, and Rc is the same as or different from each other.

In an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted tert-butyl group.

In an exemplary embodiment of the present specification, Rc is a tert-butyl group.

In an exemplary embodiment of the present specification, Rb is a polymerizable group; Or -COOH.

In an exemplary embodiment of the present specification, Rb is a polymerizable group.

In an exemplary embodiment of the present specification, Rb is -COOH.

In an exemplary embodiment of the present specification, Rb is -COOH; Or it is a compound that is any one of the following formula.

In the above structure,

L201 is a direct bond; Or -O-,

R202 and R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r202 is 1 to 3,

r203 is 1 to 5,

When r202 and 203 are each 2 or more, two or more R202 and R203 are the same as or different from each other.

In an exemplary embodiment of the present specification, L201 is -O-.

In the exemplary embodiment of the present specification, R202 and R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heterocyclic group.

In the exemplary embodiment of the present specification, R202 and R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 3 to C 20 heterocyclic group.

In the exemplary embodiment of the present specification, R202 and R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted C 3 to C 12 heterocyclic group.

In an exemplary embodiment of the present specification, R202 and R203 are each hydrogen.

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 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 g/mol to 50,000 g/mol.

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 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.

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 1% 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.

When each component contained in the solid content of the photosensitive resin composition satisfies the above content, it has strong heat resistance even at a high temperature during the color filter manufacturing process, and has an effect of preventing migration and dissolution.

The total weight of the solid content refers to the sum of the total weight of components excluding the solvent in the photosensitive 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 may further include an additive.

The additive may be one or two or more 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, a dispersant, and a leveling agent.

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 may mean 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.

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

The photosensitive 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. , Photosensitive material for overcoat layer formation, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There is no particular limitation.

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

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

The photosensitive resin composition according to an exemplary embodiment of the present specification has excellent heat resistance and has little change in color due to heat treatment, so that it is possible to provide a color filter having high color reproduction rate and high luminance and contrast ratio even by the curing process when manufacturing a color filter. I can.

The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and the type 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: 4-(4-allyl-2-(tert-butyl)phenoxy)phthalonitrile

In a 250ml round bottom flask, 50ml of dimethyl sulfoxide, 5g (28.89mmol) of 4-nitrophthalonitrile and 5.49g (28.89mmol) of 4-allyl-2-(tert-butyl)phenol were added and stirred until 80℃ while stirring. It heated up. Thereafter, 5.98g (43.34mmol) of potassium carbonate was additionally added thereto, followed by stirring for 3 hours. Thereafter, the reaction solution was added dropwise to 500 ml of DI-water to precipitate a reaction product. The precipitated precipitate was filtered under reduced pressure, recrystallized with methanol, and dried to obtain 7.5 g (26.12 mmol, 82%) of Synthesis Example 1 compound.

Synthesis Example 2: 3-(tert-butyl)-4-(3,4-dicyanophenoxy)phenethyl methacrylate

In Synthesis Example 1, 3-(tert-butyl)-4-hydroxyphenethyl methacrylate was used instead of 4-allyl-2-(tert-butyl)phenol, and the others were carried out in the same manner to obtain a compound of Synthesis Example 2.

Synthesis Example 3: 4-(2-(tert-butyl)-4-(2-(oxiran-2-ylmethoxy)ethyl)phenoxy)phthalonitrile.

In Synthesis Example 1, 2-(tert-butyl)-4-(2-(oxiran-2-ylmethoxy)ethyl)phenol was used instead of 4-allyl-2-(tert-butyl)phenol, and the others were in the same manner. Proceeding, a compound of Synthesis Example 3 was obtained.

Synthesis Example 4: 4-(2-(tert-butyl)-4-((oxetan-2-ylmethoxy)methyl)phenoxy)phthalonitrile

In Synthesis Example 1, 2-(tert-butyl)-4-((oxetan-2-ylmethoxy)methyl)phenol was used instead of 4-allyl-2-(tert-butyl)phenol, and the others were carried out in the same manner. , A compound of Synthesis Example 4 was obtained.

Synthesis Example 5: 5-allyl-2-(3,4-dicyanophenoxy)phenyl 3,5-di-tert-butyl-4-hydroxybenzoate

In Synthesis Example 1, instead of 4-allyl-2-(tert-butyl)phenol, the 5-allyl-2-hydroxyphenyl 3,5-di-tert-butyl-4-hydroxybenzoate was used, and the others were carried out in the same manner, Synthesis Example 5 A compound was obtained.

Synthesis Example 6: 4-([1,1'-biphenyl]-2-yloxy)phthalonitrile

In Synthesis Example 1, instead of 4-allyl-2-(tert-butyl)phenol, the [1,1'-biphenyl]-2-ol was used, and the others were carried out in the same manner to obtain a compound of Synthesis Example 6.

Synthesis Example 7: 4-([1,1'-biphenyl]-2-yloxy)phthalonitrile

In Synthesis Example 1, 2-cyclohexylphenol was used instead of 4-allyl-2-(tert-butyl)phenol, and the others were carried out in the same manner to obtain a compound of Synthesis Example 7.

Synthesis Example 8: 4-(4-allyl-2-cyclohexylphenoxy)phthalonitrile

In Synthesis Example 1, 4-allyl-2-cyclohexylphenol was used instead of 4-allyl-2-(tert-butyl)phenol, and the others were carried out in the same manner to obtain a compound of Synthesis Example 8.

Synthesis Example 9: Synthesis of a compound represented by Formula A

Synthesis Example 1 Compound 3g (4.41mmol), ZnCl ₂ 0.30g (2.20mmol) was added to 1-pentanol 50ml, the temperature was raised to 90 ℃ and stirred for 30 minutes. Then, 0.33g (2.20mmol) 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 MeOH 120 ml and H ₂ O 240 ml. This was separated through column chromatography to obtain Compound A prepared in Synthesis Example 9.

[Compound A] MALDI-TOF MS: 1327.56 m/z

Synthesis Example 10: Synthesis of a compound represented by Formula B

In Synthesis Example 9, 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 B prepared by Synthesis Example 10.

[Compound B] MALDI-TOF MS: 1671.71 m/z

Synthesis Example 11: Synthesis of a compound represented by Formula C

In Synthesis Example 9, 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 C prepared by Synthesis Example 11.

[Compound C] MALDI-TOF MS: 1511.58 m/z

Synthesis Example 12: Synthesis of a compound represented by Formula D

In Synthesis Example 9, 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 D prepared by Synthesis Example 12.

[Compound D] MALDI-TOF MS: 1567.64 m/z

Synthesis Example 13: Synthesis of a compound represented by Formula E

In Synthesis Example 9, 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 E prepared in Synthesis Example 13.

[Compound E] MALDI-TOF MS: 2095.87 m/z

Synthesis Example 14: Synthesis of a compound represented by Formula F

In Synthesis Example 9, 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 F prepared by Synthesis Example 13.

[Compound F] MALDI-TOF MS: 1431.61 m/z

Comparative Synthesis Example 1: 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-(3,4-dicyanophenoxy)phenethyl methacrylate

In Synthesis Example 1, 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate was used instead of 4-allyl-2-(tert-butyl)phenol, and the others Proceeding in the same manner, a compound of Comparative Example 1-1 was obtained.

Comparative Synthesis Example 2: Synthesis of the compound represented by Comparative Example 1

In Synthesis Example 9, the compound of Comparative Example 1-1 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain [Comparative Example 1] prepared in Comparative Synthesis Example 2.

[Comparative Example 1] MALDI-TOF MS: 1859.52 m/z

Comparative Synthesis Example 3: Synthesis of the compound represented by Comparative Example 2

In Synthesis Example 9, 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 [Comparative Example 2] prepared by Comparative Synthesis Example 3.

[Comparative Example 2] MALDI-TOF MS: 1247.31 m/z

Comparative Synthesis Example 4: Synthesis of the compound represented by Comparative Example 3

In Synthesis Example 9, 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 [Comparative Example 3] prepared by Comparative Synthesis Example 3.

[Comparative Example 3] MALDI-TOF MS: 1271.50 m/z

<Experimental Example>

<Preparation of photosensitive resin composition Example 1>

0.85 parts by weight of compound 1-1 prepared above, 20.78 parts by weight of binder resin A, 20.46 parts by weight of polyfunctional monomer dipentaerythritol hexaacrylate based on 100 parts by weight of the total weight of the photosensitive resin composition, photoinitiator (PBG-3057) Photosensitive resin composition Example 1 was prepared by mixing 0.68 parts by weight, 0.6 parts by weight of leveling agent F-554, 0.06 parts by weight of adhesive aid KBM-503, and 56.57 parts by weight of solvent diacetonealcohol (DAA).

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

<Production of photosensitive resin composition Examples 2 to 6>

Photosensitive resin composition Examples 2 to 6 were prepared in the same manner as in the photosensitive resin composition Example 1, except that the compound 1-1 of Example 1 was changed to the compound shown in Table 1 below.

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 compound A B C D E F

<Production of photosensitive resin composition Comparative Examples 1 to 3>

Photosensitive resin composition Comparative Examples 1 to 3 were prepared in the same manner as in the photosensitive resin composition Example 1, except that the compound of Example 1 was changed to the compound of Comparative Examples 1 to 3, respectively.

<Experimental Example>

Board fabrication

The photosensitive resin compositions prepared according to Comparative Examples and Examples 1 to 6 were spin-coated on glass (5cm X 5cm) and prebake at 100° C. for 100 seconds to form a film. After the preheat treatment, the substrate was prepared by post bake treatment at 230°C for 20 minutes.

Heat resistance evaluation

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

In addition, the post-heat treatment substrate (one post bake) was additionally treated at 230° C. for 60 minutes to obtain a transmittance spectrum in the same measurement range with the same equipment.

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

[Calculation 1]

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

A small ΔEab value indicates that the color change is small, indicating excellent heat resistance.

Comparative Example 1 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 △Eab 7.54 2.08 6.49 5.01 3.58 0.87 6.02

According to Table 2, it was confirmed that the ΔEab value of Examples 1 to 6 was smaller than the ΔEab value of Comparative Example 1. Accordingly, it was confirmed that it was possible to obtain a color filter and a color filter having excellent heat resistance by using a phthalocyanine-based dye having a specific substituent and a crosslinkable group of the present invention introduced.

Chemical resistance evaluation

The substrate was prepared by the above method, cut into 1cm × 5cm, and then immersed in 2 pieces of the cut substrate into 1cm × 5cm in 16 g of N-methyl-2-pyrrolidone solvent, followed by additional baking for 40 minutes in a convection oven at 80°C. Was carried out. The absorbance of the solvent from which the pieces of the substrate were taken out was measured, and the absorbance and the improvement rate (%) of Examples 1 to 6 compared to Comparative Example 2 are described in Table 3 below.

division Absorbance Improvement rate compared to Comparative Example 2 (%) Comparative Example 2 1.523 - Comparative Example 3 1.482 - Example 1 0.562 63.1% Example 2 0.377 75.2% Example 3 0.785 48.5% Example 4 0.269 82.3% Example 5 0.355 76.7% Example 6 0.211 86.1%

According to Table 3, it was confirmed that the absorbance of Examples 1 to 6 was smaller than the absorbance of Comparative Example 2 without a polymerizable group. The smaller the absorbance, the better the chemical resistance. Thereby, by using the phthalocyanine series pigment|dye which introduced a specific substituent and a crosslinkable group of this invention, it was able to obtain the coloring composition for color filters with improved chemical resistance by a solvent.

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,
R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or represented by the following formula A,
At least one of R1 to R4, at least one of R5 to R8, at least one of R9 to R12, and at least one of R13 to R16 are represented by the following formula A,
[Formula A]

In the formula A,

Means a moiety connected to Formula 1,
L is a direct bond; A substituted or unsubstituted alkylene group; Or -O-,
l is an integer of 0 to 3, and when l is 2 or more, L is the same as or different from each other,
Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or -OCO-R',
At least one of Ra is a substituted or unsubstituted C3 or less alkyl group; Or in the case of a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group having 3 or less carbon atoms; Or at least one of Ra that is not a substituted or unsubstituted alkoxy group is -OCO-R',
R'is a substituted or unsubstituted aryl group,
ra is an integer of 1 to 4, and when ra is 2 or more, Ra is the same as or different from each other,
Rb is a polymerizable group; Or -COOH, and rb is 0 or 1. The method according to claim 1, Ra is a substituted or unsubstituted tert-butyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted methoxy group; Or a substituted or unsubstituted phenyl group. The method of claim 1, wherein Ra is -OCO-R',
R'is a substituted or unsubstituted phenyl group. The compound of claim 1, wherein Ra is represented by the following formula B:
[Formula B]

In Formula B,

Means a moiety connected to the formula A,
Rc is hydrogen; heavy hydrogen; Or a substituted or unsubstituted tert-butyl group,
rc is an integer of 2 to 4, and Rc is the same as or different from each other. The method of claim 1, wherein Rb is -COOH; Or any one of the following formulas:

In the above structure,
L201 is a direct bond; Or -O-,
R202 and R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r202 is 1 to 3,
r203 is 1 to 5,
When r202 and 203 are each 2 or more, two or more R202 and R203 are the same as or different from each other. 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 1% 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.