KR20200038707A - Coloring material composition, photosensitive resin composition, photoresist, color filter, display device comprising the same - Google Patents

Abstract

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

Description

Color material composition, photosensitive resin composition, photosensitive material, color filter, display device {COLORING MATERIAL COMPOSITION, PHOTOSENSITIVE RESIN COMPOSITION, PHOTORESIST, COLOR FILTER, DISPLAY DEVICE COMPRISING THE SAME}

This specification relates to a colorant composition. In addition, the present specification relates to a photosensitive resin composition comprising the colorant composition, a photosensitive material prepared using the same, a color filter, and a display device including the same.

Recently, in the color filter, the necessity for a product for high brightness (transmission) has been continuously demanded, but at present, it has reached a limit as a composition for improving dispersibility of existing materials and preventing a decrease in luminance.

In the case of Red Photoresist, a product with a high luminance target was developed using a combination of commercially available color materials, but large luminance improvement is not currently achieved. Development of a new red colorant to increase the transmittance should be made, but the red colorant that increases the transmittance has a problem that the absorption range is narrow. Therefore, it is necessary to develop a complementary color material to effectively absorb the region of 380 nm to 550 nm.

Korean Patent Publication No. 2001-0009058

This specification intends to provide a colorant composition, a photosensitive resin composition comprising the colorant composition, a photosensitive material prepared using the colorant, a color filter, and a display device including the same.

An exemplary embodiment of the present specification provides a color material composition comprising a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

R1 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -CONH-R ',

R 'is a substituted or unsubstituted aryl group,

R2 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R3 is hydrogen; Halogen group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r2 is an integer from 0 to 4, and when r2 is 2 or more, 2 or more R2s are the same as or different from each other,

r3 is an integer from 1 to 3, and when r3 is 2 or more, 2 or more R3s are the same or different from each other.

An exemplary embodiment of the present specification, the color material composition; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.

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

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

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

When the colorant composition according to the present specification is applied to a color filter, the maximum absorption wavelength is shorter than that of the conventional red colorant, thereby effectively absorbing the maximum absorption wavelength range of 380 nm to 550 nm, thereby narrow absorption of the high-transmission red colorant Effectively complement the scope.

Accordingly, when the colorant composition according to the present specification is applied to a high-transmission red color filter, it can serve as a complementary colorant for the red color.

In addition, the color material composition according to the present specification is excellent in heat resistance.

In addition, the colorant composition comprising the compound according to the present specification has low transmittance in the maximum absorption wavelength range, and thus, when manufacturing the color filter using the colorant composition, the content of the input colorant can be reduced.

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

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

In the present specification, when a part “includes” a certain component, this means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

An exemplary embodiment of the present specification provides a color material composition comprising a compound represented by the formula (1).

In an exemplary embodiment of the present specification, when a color material composition including the compound represented by Chemical Formula 1 is applied to a color filter, specifically, when applied to a high transmittance red color filter, it may serve as a complementary color material of a red color.

Specifically, when the compound represented by Chemical Formula 1 has a maximum absorption wavelength between 380 nm and 450 nm, it may be used as a yellow-based color filter. In addition, when the compound represented by Formula 1 has a maximum absorption wavelength between 450 nm and 550 nm, it can be used as an orange-based color filter. As described above, the color material composition including the compound represented by Chemical Formula 1 may serve as a complementary color material of red color.

In addition, the present invention, by including the compound represented by the formula (1) in the colorant composition, it is possible to easily adjust the absorption range, solubility and heat resistance. Specifically, when a bulky alkyl group is substituted for nitrogen (N) of the core structure of Formula 1, solubility of the compound represented by Formula 1 may be increased. In addition, when an aryl group is substituted with nitrogen (N) of the core structure of Chemical Formula 1, heat resistance may be enhanced without affecting color characteristics.

Due to the above-described advantage of increasing solubility, it is possible to prevent agglomeration between color materials, and through this, the amount of material required for color material dispersion can be reduced.

The colorant composition comprising the compound according to the present specification has a low transmittance in the maximum absorption wavelength range, and thus the content of the colorant input when manufacturing the color filter using the colorant composition can be reduced.

According to the exemplary embodiment of the present specification, when the linker and the moiety forming a carbon-carbon bond in a thiophene group in the core structure of Chemical Formula 1, the maximum absorption wavelength is shifted to the substance The light absorbing region of can be easily adjusted and excellent heat resistance can be expected.

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

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

Means a site that is attached to another substituent or linkage.

The bonding portion means a portion connected between chemical formulas or chemical structures.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Carboxyl period; Imide group; Amide group; Alkoxy groups; Alkyl groups; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Sulfonate groups; Amine group; Aryl group; Heteroaryl group; Silyl group; Alkyl sulfoxy group; Aryl sulfoxyl group; Boron group; Acryloyl group; Acrylate groups; Ether group; And one or more substituents selected from the group containing a heterocyclic group including one or more of N, O, S or P atoms, or having no substituents.

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

In the present specification, the alkyl group may be a straight chain or a branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox Tilgi, and the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 10 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

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

In the present specification, the 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 cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group include a cyclopentenylene group and a cyclohexenylene group, but are not limited to these.

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

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with 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 heteroatom as a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but has 2 to 30 carbon atoms, and specifically 2 to 20 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil 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 Flags, etc., but are not limited to these.

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

In this specification, the silyl group may be represented by the formula of -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited to this.

In the present specification, the alkyl sulfoxy group includes methyl sulfoxy group, ethyl sulfoxyl group, propyl sulfoxyl group, butyl sulfoxyl group, but is not limited thereto. The alkyl group in the alkyl sulfoxy group can be applied to the description of the aforementioned alkyl group.

In the present specification, the aryl sulfoxy group includes benzene sulfoxy group, p-toluene sulfoxy group, and the like, but is not limited thereto. The aryl group in the aryl sulfoxy group may be applied to the aryl group described above.

In the present specification, the boron group may be represented by the formula -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

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

In the present specification, the acrylate group means a photopolymerizable unsaturated group, for example, (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 '(meth) acrylate' has the same meaning.

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

In the present specification, the cycloalkylene group means that the cycloalkane has two bonding positions. The number of carbon atoms of the cycloalkylene group is not particularly limited, but the description of the cycloalkyl group described above may be applied.

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

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.

로 표시될 수 있다. In the present specification, the keto group

It may be indicated by.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent, and is represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same or different from each other. And each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl group; Alkoxy groups; Cycloalkyl group; Aryl group; And a heterocyclic group. However, at least one of R ₁₀₇ and R ₁₀₈ is not hydrogen. For example, -NH ₂ ; Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In the present specification, "divalent" means that there are two binding positions.

In one embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -CONH-R ', wherein R' is a substituted or unsubstituted aryl group.

When R1 is a non-hydrogen substituent and the molecular weight is increased, when the compound represented by Chemical Formula 1 is applied to a colorant composition, heat resistance and / or solubility in a solvent may increase. This is because the substituent of R1 becomes bulky, the distance between the compounds represented by the formula (1) increases, and agglomeration does not occur, thereby increasing the dispersion degree in the solvent.

In one embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or -CONH-R '.

In one embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or -CONH-R '.

In one embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms; Or -CONH-R '.

In one embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group; Or -CONH-R '.

In one embodiment of the present specification, R1 is hydrogen; A methyl group substituted with a phenyl group; A propyl group substituted with a phthalimide group (Phthalimide); A pentyl group substituted with sodium bromide (NaBr); A hexyl group substituted with an ethyl group; A phenyl group unsubstituted or substituted with chlorine; Or naphthyl group; Or -CONH-R '.

May be combined with the sodium cation (Na ⁺⁾ ions ^- The sodium bromide (NaBr) is bromo can be represented by folk sodium, bromine anions (Br).

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

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

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

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

In one embodiment of the present specification, R 'is a phenyl group.

In one embodiment of the present specification, R2 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R2 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R2 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R2 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, R2 is hydrogen; bromine; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R2 is hydrogen; bromine; A methyl group substituted with fluorine; Or a phenyl group unsubstituted or substituted with fluorine.

In one embodiment of the present specification, R2 is hydrogen; bromine; Trifluoromethyl group (-CF ₃ ); Or a phenyl group unsubstituted or substituted with fluorine.

In one embodiment of the present specification, R3 is hydrogen; Halogen group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R3 is hydrogen; Halogen group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; Halogen group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; Halogen group; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; Halogen group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted benzothiadiazole group; Or a substituted or unsubstituted benzodithiophene group.

In one embodiment of the present specification, R3 is hydrogen; bromine; Chlorine, bromine, substituted or unsubstituted methyl groups, substituted or unsubstituted n-propyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclohexyl groups, substituted Or an unsubstituted carbazole group, a substituted or unsubstituted oxidole, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted arylamine group-substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with a thiophene group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, r2 is an integer from 0 to 4, and when r2 is 2 or more, two or more R2s are the same or different from each other, r3 is an integer from 1 to 3, and when r3 is 2 or more, R3 or more. Are the same or different from each other.

According to another exemplary embodiment of the present specification, Chemical Formula 1 provides a coloring material composition including a compound represented by Chemical Formula 2.

[Formula 2]

In Chemical Formula 2,

R1, R2, r1 and r2 are the same as defined in Formula 1 above,

R4 is hydrogen; Or a halogen group,

r4 is an integer from 0 to 2, and when r4 is 2, R4 is the same or different from each other,

L1 is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; Or -A1-A2-A1,

A1 is a substituted or unsubstituted arylene group,

A2 is a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group,

A is hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; Or -A1-A2-A1, A1 is a substituted or unsubstituted arylene group, and A2 is a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group.

In one embodiment of the present specification, R4 is hydrogen.

In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; Or -A1-A2-A1.

In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; Or -A1-A2-A1.

In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms; Or -A1-A2-A1.

In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 12 carbon atoms; A substituted or unsubstituted heteroarylene group having 2 to 12 carbon atoms; Or -A1-A2-A1.

In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted divalent benzothiazole group; A substituted or unsubstituted divalent benzodithiophene group; Or -A1-A2-A1.

In one embodiment of the present specification, L1 is a direct bond; A phenylene group unsubstituted or substituted with fluorine; Biphenylene group; A fluorenylene group unsubstituted or substituted with an octyl group or a keto group; Naphthylene group; Or -A1-A2-A1.

In one embodiment of the present specification, A1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A1 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, A1 is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

In one embodiment of the present specification, A1 is a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, A1 is a phenylene group.

In one embodiment of the present specification, A2 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; Or a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms.

In one embodiment of the present specification, A2 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; Or a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms.

In one embodiment of the present specification, A2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms.

In one embodiment of the present specification, A2 is a substituted or unsubstituted propylene group; Or a substituted or unsubstituted cyclohexylene group.

In one embodiment of the present specification, A2 is an n-propylene group; Isopropylene group; Or a cyclohexylene group.

In one embodiment of the present specification, A is hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, A is hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In one embodiment of the present specification, A is hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.

In one embodiment of the present specification, A is hydrogen; bromine; Goat; A substituted or unsubstituted biphenylamine group; A substituted or unsubstituted methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophene group; It is a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, A is hydrogen; bromine; Goat; Biphenylamine group; Trifluoromethyl group; A phenyl group unsubstituted or substituted with a fluorine, chlorine, trifluoromethyl group, tert-butyl group, biphenylamine group, carbazole group or naphthyl group; Naphthyl group; A fluorenyl group substituted with a keto group; A thiophene group substituted or unsubstituted with a substituted or unsubstituted oxindole; Or carbazole.

According to another exemplary embodiment of the present specification, Chemical Formula 2 provides a colorant composition including the compound represented by Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

R1, R2, R4, r1, r2, r4 and L1 are the same as defined in Formula 2,

R5 is hydrogen; Or a halogen group,

r5 is an integer from 0 to 2, and when r5 is 2, two R5s are the same or different from each other,

R11 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -CONH-R ',

R 'is a substituted or unsubstituted aryl group,

R22 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

r22 is an integer from 0 to 4, and when r22 is 2 or more, two or more R22s are the same or different from each other.

In one embodiment of the present specification, R5 is hydrogen.

In one embodiment of the present specification, R11 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -CONH-R '.

In one embodiment of the present specification, R11 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or -CONH-R '.

In one embodiment of the present specification, R11 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; Or -CONH-R '.

In one embodiment of the present specification, R11 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; Or -CONH-R '.

In one embodiment of the present specification, R11 is hydrogen; A substituted or unsubstituted propyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted phenyl group; Or -CONH-R '.

In one embodiment of the present specification, R11 is hydrogen; A propyl group substituted with a phthalimide group; A pentyl group substituted with an ethyl group or sodium bromide; A hexyl group substituted with an ethyl group; Phenyl group; Or -CONH-R '.

In one embodiment of the present specification, R 'is as described above.

In one embodiment of the present specification, R22 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R22 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R22 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, R22 is hydrogen.

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

In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum absorption wavelength between 380 nm and 550 nm.

In another exemplary embodiment, the compound represented by Chemical Formula 1 has a maximum absorption wavelength between 450 nm and 550 nm.

Specifically, the compound represented by Chemical Formula 3 may have a maximum absorption wavelength between 450 nm and 550 nm.

Having a maximum absorption wavelength between 450 nm and 550 nm means that the compound represented by Chemical Formula 1 can be used as an orange-based color filter as a complementary color material for a red color filter.

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

According to an exemplary embodiment of the present specification, the colorant composition may include only the compound represented by the formula (1).

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

An exemplary embodiment of the present specification is the colorant composition; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising at least one selected from the group consisting of a solvent.

An exemplary embodiment of the present specification is the colorant composition; Binder resin; Leveling agents; Adhesive aids; And it provides a photosensitive resin composition comprising a solvent.

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

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

Polyfunctional monomers that impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

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

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro styrene. It may be selected from the group consisting, but is not limited to these.

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

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

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

The monomer that gives the alkali solubility is not particularly limited as long as it contains an acid group, for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate It is preferable to use one or more, but is not limited to these.

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

In one embodiment of the present specification, the binder resin may be a copolymer having a mass ratio of benzyl methacrylate; N-phenylmaleimide; styrene; methacrylic acid = 55: 9: 11: 25.

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

The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate It may be a species or a mixture of two or more.

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

The acetophenone-based compounds are 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoinmethyl ether, benzoinethyl ether, benzoinisobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, and the like.

The biimidazole-based compound is 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , But is not limited to this.

The triazine-based compound is 3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4 -Bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} acetate, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, benzyl-2- {4- [ 2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionamide, 2,4-bis (trichloro Methyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like. .

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

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

In one embodiment of the present specification, the solvent may be dimethylformamide (DMF).

In one embodiment of the present specification, the colorant composition is 0.1 to 60 parts by weight, the binder resin is 1 to 85 parts by weight, and the solvent is 10 to 60 parts by weight based on 100 parts by weight of the photosensitive resin composition. Provided is a composition.

In one embodiment of the present specification, the photosensitive resin composition may further include 0.01 to 10 parts by weight of the leveling agent and 0.01 to 10 parts by weight of the adhesive agent based on 100 parts by weight of the photosensitive resin composition.

In one embodiment of the present specification, the photosensitive resin composition may further include 0.5 to 10 parts by weight of the photoinitiator and 5 to 30 parts by weight of the multifunctional monomer based on 100 parts by weight of the photosensitive resin composition.

In one embodiment of the present specification, based on the total weight of the photosensitive resin composition, the content of the colorant composition is 1 to 50% by weight; The content of the binder resin is 5 to 30% by weight; The content of the photoinitiator is 0.5 to 10% by weight; The content of the polyfunctional monomer is 5 to 30% by weight; And the content of the solvent is 10 to 60% by weight.

According to an exemplary embodiment of the present specification, based on the total weight of the solid content in the photosensitive resin composition, the content of the coloring material composition is 5% 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, 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 the components excluding the solvent in the photosensitive resin composition. The basis of the solid content and the weight percentage based on the solid content of each component can be measured by general analytical means used in the art, such as liquid chromatography or gas chromatography.

According to one embodiment of the present specification, the photosensitive resin composition may further include an antioxidant.

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

One embodiment of the present specification is a leveling agent; Adhesive aids; Surfactants; And it provides a photosensitive resin composition that further comprises at least one selected from the group consisting of antioxidants.

One embodiment of the present specification provides a photosensitive resin composition further comprising a leveling agent and an adhesion aid.

In the present specification, the leveling agent, adhesion aid, and surfactant are included in the additive.

According to an exemplary embodiment of the present specification, the photosensitive resin composition further comprises one or more additives selected from the group consisting of a photocrosslinking agent, a curing accelerator, an adhesion promoter, a thermal polymerization inhibitor, an ultraviolet absorber, and a dispersing agent .

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

The photocrosslinking agent is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Florenone-based compounds, such as 9-Florenone, 2-Croro-9-Prorenone, and 2-methyl-9-Florenone; Thioxanthone series such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane, etc. Acridine compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptan-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzo Coumarin-based compounds such as pyrano [6,7,8-ij] -quinolinazine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azide benzal acetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of;

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

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

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used. DIC is a fluorine-based surfactant. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.

The antioxidant may be at least one selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethylphosphate or triethylphosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-butylphenol) or bis [3 , 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol esters such as hindered phenol primary antioxidants; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine Secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuramdisulfide tetrabis [methylene-3- (laurylthio) propionate] methane Secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4 ' And phosphite-based secondary antioxidants such as -Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

In one embodiment of the present specification, as the adhesion aid, those commonly used in the art may be used, and as an example, there is KBM-503, but is not limited thereto.

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

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- Methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and is not limited to sugar technology These may include those commonly known in the art.

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

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

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

In the present specification, the leveling agent may be F-554.

According to an exemplary embodiment of the present specification, to provide a photosensitive material prepared using the photosensitive resin composition.

In more detail, the photosensitive resin composition of the present specification is coated on a substrate by an appropriate method and cured to form a thin film or patterned photosensitive material.

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

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

The photosensitive resin composition according to the present specification is a thin film transistor type liquid crystal display (TFT LCD) pigment dispersion type photosensitive material for manufacturing a color filter, a thin film transistor liquid crystal display device (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode , Can be used for photoresist for overcoat layer formation, column spacer photoresist, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There are no restrictions.

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

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

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

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

A black pattern on a grid called a black matrix can be arranged between color pixels of a 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 may be used. However, considering the high cost of the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, it is possible to use a resin black matrix by a pigment dispersion method capable of fine processing.

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

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

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

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

<Example>

<Synthesis Examples of Colorant Compound>

[Production Example 1: Preparation of Compound A]

Oxindole (1.96 g, 14.7 mmol, 1.4 eq), 5-Bromo-2-thiophenecarboxaldehyde (2.00 g, 10.5 mmol, 1.0 eq), ethyl alcohol 50 ml was added to a 250 mL 2-neck round-bottom flask, followed by stirring. Ordered. Piperidine 1ml was added dropwise and refluxed for 24 hours. The solvent was evaporated using a rotary evaporator and recrystallized with methyl alcohol. The resulting precipitate was filtered under reduced pressure, washed 3 times with methyl alcohol, and then dried in a vacuum oven at 80 ° C. to obtain compound [A] (2.40 g, 7.84 mmol, 74.7%).

Ionization mode: APCI +: m / z = 306 [M + H] +, Exact Mass: 304.95

[Production Example 2: Preparation of Compound A-1]

[A] (1.00g, 3.27mmol, 1.0eq) and anhydrous potassium carbonate (1.36g, 9.81mmol, 3eq) were added to a 250mL 2-neck round-bottom flask and dissolved in 30ml of anhydrous dimethylformamide (DMF). The mixture was stirred at 120 ° C. for 1 hour, 2-ethylhexyl bromide (0.95 g, 4.91 mmol, 1.5 eq) was added dropwise, and then reacted for 24 hours. After the reaction, DMF (anhydrous dimethylformamide) was removed and extracted with methylene chloride. After concentration and recrystallization with methyl alcohol, washed with methyl alcohol and hexane and dried to obtain the product [A-1] (0.78 g, 1.86 mmol, 57.0%).

Ionization mode: APCI +: m / z = 418 [M + H] +, Exact Mass: 417.08

[Production Example 3: Preparation of Compound B]

[A] (0.31g, 1mmol, 1eq) and 4- (Trifluoromethyl) benzeneboronic acid (0.38g, 2mmol, 2eq) were added to a 250mL 2-neck round-bottom flask and dissolved in 7ml of Tetrahydrofuran (THF). Potassium carbonate (0.69 g, 5 mmol, 5 eq) was dissolved in 3 ml of distilled water and Tetrakis (triphenylphosphine) palladium (0) (35 mg, 3 mol%) was added and refluxed while stirring vigorously for 24 hours under a nitrogen atmosphere. After the reaction was completed, the solvent was removed and extracted, followed by filtering with Magnesium sulfate. Recrystallized with Methylene chloride and methyl alcohol, filtered and dried to obtain compound [B] (0.23g, 0.62mmol, 61.9%).

Ionization mode: APCI +: m / z = 372 [M + H] +, Exact Mass: 371.06

[Production Example 4: Preparation of compound C-1]

Add [A-1] (0.48g, 1.16mmol, 2.4eq), Benzene-1,4-diboronic acid (0.08g, 0.48mmol, 1.0eq) to a 250mL 2-neck round bottom flask in 60ml of tetrahydrofuran (THF) Melted. Potassium carbonate (0.33g.40mmol, 5eq) was dissolved in 10ml of distilled water and Tetrakis (triphenylphosphine) palladium (0) (17mg, 3 mol%) was added and refluxed with strong stirring for 24 hours under a nitrogen atmosphere. After the reaction was completed, the solvent was removed and extracted, followed by purification by silica chromatography. The solvent was removed and dried to obtain compound [C-1] (0.29 g, 0.38 mmol, 78.9%).

Ionization mode: APCI +: m / z = 753 [M + H] +, Exact Mass: 752.35

[Production Example 5: Preparation of compound B-1]

Into a 250 mL 2-neck round bottom flask [B] (0.15 g, 0.40 mmol, 1 eq) and anhydrous potassium carbonate (0.17 g, 1.20 mmol, 3 eq) were added and dissolved in 5 ml of anhydrous dimethylformamide (DMF). The mixture was stirred at 100 ° C. for 1 hour, N- (3-Bromopropyl) phthalimide (0.13 g, 0.49 mmol, 1.2 eq) was added dropwise and reacted for 18 hours. After the reaction, DMF (anhydrous dimethylformamide) was removed and extracted with methylene chloride. Recrystallized with methyl alcohol, washed with methyl alcohol and dried to obtain the product [B-1] (0.13g, 0.22mmol, 55.2%).

Ionization mode: APCI +: m / z = 589 [M + H] +, Exact Mass: 588.12

[Production Example 6: Preparation of compound B-2]

In a 250mL 2-neck round-bottom flask [A] (0.50g, 1.63mmol, 1eq), 2- (tributylstannyl) thiophene (0.73g, 1.96mmol, 1.2eq), tetrakis (triphenylphosphine) palladium (0) (47mg, 2.5 mol%) and dissolve in 17 ml of anhydrous toluene. It was refluxed for 18 hours under a nitrogen atmosphere. After the reaction, the solvent was removed, recrystallized with methylene chloride and methyl alcohol, filtered and washed. After drying, [B-2] (0.38 g, 1.23 mmol, 75.3%) was obtained.

Ionization mode: APCI +: m / z = 310 [M + H] +, Exact Mass: 309.03

[Production Example 7: Preparation of Compound A-2]

[A] (0.91g, 3.0mmol, 1.0eq), anhydrous potassium carbonate (1.24g, 9.0mmol, 3eq), anhydrous dimethylformamide (DMF) 30ml N- (3-Bromopropyl) phthalimide (0.97g, 3.6mmol, 1.2eq ) Was performed in the same manner as in the synthesis method of Compound B-1 of Preparation Example 5 to obtain [A-2] (1.09 g, 2.2 mmol, 73.6%).

Ionization mode: APCI +: m / z = 493 [M + H] +, Exact Mass: 492.01

[Production Example 8: Preparation of compound C-2]

[A-2] (1.0g, 2.0mmol, 2.2eq), Benzene-1,4-diboronic acid (0.15g, 0.91mmol, 1.0eq), tetrahydrofuran (THF) 100ml, Potassium carbonate (0.63g.4.55mmol, 5eq), 14ml of distilled water, tetrakis (triphenylphosphine) palladium (0) (32mg, 3 mol%) was carried out in the same manner as in the synthesis method of compound C-1 of Preparation Example 4 [C-2] (0.56g, 0.62mmol , 68.1%).

Ionization mode: APCI +: m / z = 903 [M + H] +, Exact Mass: 902.22

[Production Example 9: Preparation of Compound B-4]

In a 250 mL 2-neck round-bottom flask, oxindole (1.33 g, 10.0 mmol, 2.0 eq), 2,2-bithiophene-5,5-dicarbaldehyde (1.11 g, 5.0 mmol, 1.0 eq) was added to ethyl alcohol 35 ml, piperidine 0.5 ml. I put it. The precipitate formed by refluxing for 24 hours was obtained by cooling to room temperature and filtering. Washed with ethyl alcohol and dried in a vacuum oven to obtain compound [B-3] (2.24g, 4.95mmol, 99.0%). [B-3] was used in the next reaction without further purification because of poor solubility.

[B-3] (0.45g, 1.0mmol, 1.0eq) and anhydrous potassium carbonate (0.41g, 3.0mmol, 3eq) were added to a 250mL 2-neck round bottom flask and dissolved in 30ml of anhydrous dimethylformamide (DMF). The mixture was stirred at 120 ° C. for 1 hour, 2-ethylhexyl bromide (0.58 g, 3.0 mmol, 3.0 eq) was added dropwise, and then reacted for 24 hours. After the reaction, DMF was removed and extracted with methylene chloride. After purification by silica chromatography, it was recrystallized with methyl alcohol and filtered. Drying gave [B-4] (0.18 g, 0.27 mmol, 26.5%).

Ionization mode: APCI +: m / z = 677 [M + H] +, Exact Mass: 676.32

Compound of Comparative Example 1

[Production Example 10: Preparation of Comparative Example Compound]

8-aminoquinaldine (1.58g, 10.0mmol, 2.5eq) was added to a 250mL 2-neck round-bottom flask, dissolved in a solvent mixed with 36% HCl (4g, 30.0mmol, 7.5eq) and 50ml of DI water and heated to 50 ℃. Did. The temperature was reduced to 0 ° C with an ice bath, and NaNO ₂ (1.04 g, 15.0 mmol) was dissolved in 3 ml of DI water and added dropwise to the reaction. NaOH (1.44 g, 36 mmol) and 3-hydroxy-2-naphthanilide (1.05 g, 4.0 mmol, 1.0 eq) were dissolved in 20 ml DI water and added dropwise to the reaction. The pH was neutralized to 6.0-8.0, filtered and washed with water. After drying, it was recrystallized from MeOH. It was dried to obtain the [Comparative Example] compound (0.51 g, 1.18 mmol, 29.5%).

Ionization mode: APCI +: m / z = 433 [M + H] +, Exact Mass: 432.16

<Production of Example Photosensitive Resin Composition>

Example 1

Based on 100 parts by weight of the total weight of the photosensitive resin composition, 0.4 parts by weight of the colorant composition containing the compound A-2, 78.18 parts by weight of binder resin A, 0.6 parts by weight of F-554 leveling agent, 0.08 parts by weight of adhesive aid KBM-503, solvent (DMF, Dimethylformamide) 20.74 parts by weight of the mixture to prepare a photosensitive resin composition Example 1.

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

Examples 2 to 5

Photosensitive resin compositions 2 to 5 were prepared in the same manner as in Example 1, except that Compound A-2 in Example 1 was changed to a compound in Table 1 below.

<Production of the photosensitive resin composition of Comparative Example>

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

Comparative Example 1 Example 1 Example 2 Example 3 Example 4 Example 5 compound Comparative example A-2 B-1 B-4 C-1 C-2

<Experimental Example>

Substrate production

The photosensitive resin compositions prepared by Examples 1 to 5 and Comparative Example 1 were spin coated on glass (5 cm X 5 cm) and subjected to preheating at 100 ° C. for 100 seconds to form a film. After pre-heat treatment, the substrate was produced by post-baking at 230 ° C for 20 minutes.

Absorption wavelength and heat resistance evaluation

The absorption spectrum in the wavelength range of 380 nm to 780 nm was obtained by using a substrate (post bake 1 time) produced by the substrate manufacturing method using a spectrometer (MCPD, Otsuka Co.).

In addition, the prepared post-heat treatment substrate (1 post bake) was additionally treated at 230 ° C. for 100 minutes to obtain a transmittance spectrum in the same measuring range as the same equipment.

The heat resistance (ΔEab) was calculated by the following Equation 1 using the values L *, a *, and b * obtained from the absorption spectrum obtained using the C light source as a backlight, and is shown in Table 2 below.

[Calculation formula 1]

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

A small ΔEab value means that there is little color change, indicating excellent heat resistance.

In addition, the maximum absorption wavelength measurement results are shown in Table 2 below.

Heat resistance (△ Eab) Maximum absorption wavelength (nm) Comparative Example 1 16.4 523 Example 1 7.5 381 Example 2 6.8 396 Example 3 7.9 504 Example 4 3.7 467 Example 5 3.4 465

According to Table 2, it was confirmed that the ΔEab values of Examples 1 to 5 were smaller than those of Comparative Example 1, and the heat resistance of Examples 1 to 5 was excellent.

In addition, it was confirmed that the maximum absorption wavelength range of Examples 1 to 5 satisfies the wavelength range of 380 nm to 550 nm, so that it can serve as a complementary color material for the high-transmission red color filter desired in this specification.

Particularly, as in Examples 3 to 5, the colorant composition according to the present specification can be used as an orange-based color filter from a maximum absorption wavelength at 450 nm to 550 nm, thereby becoming a complementary colorant of red color. Was confirmed.

Permeability evaluation

The post-heat treatment (post bake 1 time) substrate manufactured under the above conditions was measured using a spectrometer (MCPD, Otsuka Co.) to measure the transmittance at the maximum absorption wavelength.

Permeability after PB 1 time (%) Comparative Example 1 48.1 Example 1 36.6 Example 2 32.5 Example 3 20.3 Example 4 23.4 Example 5 23.1

According to Table 3, it was confirmed that the transmittances of Examples 1 to 5 were lower than those of Comparative Example 1.

When the embodiment according to the present specification has excellent heat resistance as shown in Table 2, satisfies the maximum absorption wavelength range, and satisfies the lower transmittance than Comparative Example 1, when applied to the high-transmission red color filter desired in this specification , It was confirmed that it can sufficiently serve as a complementary color material capable of effectively absorbing a wavelength region of 380 nm to 550 nm.

Specifically, when the transmittance of Examples 1 to 5 is lower than that of Comparative Example 1, when combining color materials for color filters, it means that there is an advantage that the content of the input color material can be relatively reduced.

In addition, Examples 4 and 5, as compared to Comparative Example 1, due to the large difference in ΔEab value, it was confirmed that the heat resistance is excellent in the number of sheets. That is, it was confirmed that Examples 4 and 5 can be used as a complementary color material of a red color filter because of having excellent heat resistance and having a maximum absorption wavelength at 450 nm to 550 nm.

In addition, it was confirmed that the heat resistance increased as the molecular weight of the compound represented by Formula 1 increased.

Claims (12)

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

In Chemical Formula 1,
R1 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -CONH-R ',
R 'is a substituted or unsubstituted aryl group,
R2 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R3 is hydrogen; Halogen group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r2 is an integer from 0 to 4, and when r2 is 2 or more, 2 or more R2s are the same as or different from each other,
r3 is an integer from 1 to 3, and when r3 is 2 or more, 2 or more R3s are the same or different from each other. The method according to claim 1, wherein the compound represented by Formula 1 is a colorant composition that is a compound represented by the following Formula 2:
[Formula 2]

In Chemical Formula 2,
R1, R2, r1 and r2 are the same as defined in Formula 1 above,
R4 is hydrogen; Or a halogen group,
r4 is an integer from 0 to 2, and when r4 is 2, R4 is the same as or different from each other,
L1 is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; Or -A1-A2-A1,
A1 is a substituted or unsubstituted arylene group,
A2 is a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group,
A is hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The method according to claim 2, wherein the compound represented by the formula (2) is a colorant composition that is a compound represented by the formula (3):
[Formula 3]

In Chemical Formula 3,
R1, R2, R4, r1, r2, r4 and L1 are the same as defined in Formula 2,
R5 is hydrogen; Or a halogen group,
r5 is an integer from 0 to 2, and when r5 is 2, two R5s are the same or different from each other,
R11 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -CONH-R ',
R 'is a substituted or unsubstituted aryl group,
R22 is hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
r22 is an integer from 0 to 4, and when r22 is 2 or more, two or more R22s are the same or different from each other. The method according to claim 2,
L1 is a substituted or unsubstituted arylene group; A substituted or unsubstituted heteroarylene group; Or -A1-A2-A1,
A1 is a substituted or unsubstituted arylene group,
A2 is a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group. The method according to claim 1, wherein the compound represented by Formula 1 is a colorant composition comprising a compound represented by any one of the following formula:

The method according to claim 1, wherein the compound represented by Formula 1 is a colorant composition having a maximum absorption wavelength between 380nm to 550nm. The color material composition according to any one of claims 1 to 6; Binder resin; Polyfunctional monomers; Photoinitiators; And Photosensitive resin composition comprising at least one selected from the group consisting of a solvent. The method according to claim 7, Leveling agent; Adhesive aids; Surfactants; And one or more selected from the group consisting of antioxidants. The photosensitive resin composition according to claim 7, wherein the colorant composition is 0.1 to 60 parts by weight, the binder resin is 1 to 85 parts by weight, and the solvent is 10 to 60 parts by weight based on 100 parts by weight of the photosensitive resin composition. A photosensitive material prepared using the photosensitive resin composition according to claim 7. A color filter comprising the photosensitive material according to claim 10. Display device comprising a color filter according to claim 11.